Modular synthesis of polyene side chain analogues of the potent macrolide antibiotic … ·...
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1 Electronic Supplementary Information (ESI) Modular synthesis of polyene side chain analogues of the potent macrolide antibiotic etnangien by a flexible coupling strategy based on hetero-bis-metallated alkenes† Mario Altendorfer, a Aruna Raja, b Florenz Sasse, b Herbert Irschik c and Dirk Menche a,d, * a University of Heidelberg, Department of Organic Chemistry, INF 270, D-69120 Heidelberg, Germany, EU. b Helmholtz Centre for Infection Research, Department of Chemical Biology, Inhoffenstr. 7, 38124 Braunschweig, Germany, EU. c Helmholtz Centre for Infection Research, Research Group Microbial Drugs, Inhoffenstr. 7, 38124 Braunschweig, Germany, EU. d University of Bonn, Kekulé-Department of Organic Chemistry and Biochemistry, Gerhard-Domagk- Str. 1, D-53121 Bonn, Germany, EU. E-mail: [email protected] Contents Copies of 1 H and 13 C NMR spectra. Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2012
Transcript of Modular synthesis of polyene side chain analogues of the potent macrolide antibiotic … ·...
1
Electronic Supplementary Information (ESI)
Modular synthesis of polyene side chain analogues of the potent
macrolide antibiotic etnangien by a flexible coupling strategy
based on hetero-bis-metallated alkenes†
Mario Altendorfer,a Aruna Raja,b Florenz Sasse,b Herbert Irschikc and Dirk Menchea,d,*
a University of Heidelberg, Department of Organic Chemistry, INF 270, D-69120 Heidelberg,
Germany, EU.
b Helmholtz Centre for Infection Research, Department of Chemical Biology, Inhoffenstr. 7, 38124
Braunschweig, Germany, EU.
c Helmholtz Centre for Infection Research, Research Group Microbial Drugs, Inhoffenstr. 7, 38124
Braunschweig, Germany, EU.
d University of Bonn, Kekulé-Department of Organic Chemistry and Biochemistry, Gerhard-Domagk-
Str. 1, D-53121 Bonn, Germany, EU.
E-mail: [email protected]
Contents
Copies of 1H and 13C NMR spectra.
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
2
c081120dmma.23_001001r
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
Chemical Shift (ppm)
Bu3Sn OH
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
16a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
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c081120dmma.23.003.001.1r.esp
144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
Bu3Sn OH
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
16a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
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c110408dmma.375_II_001001r
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
Bu3Sn OH
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
16b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
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a110404dmma375_2_002001r
152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
Bu3Sn OH
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
16b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
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b081117dmma.28_001001r
6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
Chemical Shift (ppm)
Bu3SnOH
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
16c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
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b081117dmma.28_002001r
145 140 135 130 125 120 115 110 105 100 95 90 85 80 75 70 65 60 55 50 45 40 35 30 25 20 15 10 5
Chemical Shift (ppm)
Bu3SnOH
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
16c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
8
d080725dmma.2_001001r
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
Bu3Sn OH
solvent: CDCl3 nucleus: 1H frequency: 500.130 MHz
16d
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
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d080725dmma.2.003.001.1r.esp
144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
OHBu3Sn
solvent: CDCl3 nucleus: 13C frequency: 125.78 MHz
16d
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
10
b101210dmma.308-III_002001r
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
Chemical Shift (ppm)
Bu3Sn OH
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
16e
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
11
b101210dmma.308-III.001.001.1r.esp
144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
OHBu3Sn
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
16e
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
12
c101214dmma.309-II_002000fid
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
Chemical Shift (ppm)
Bu3Sn OH
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
16f
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
13
c101214dmma.309-II.001.esp
144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
Bu3Sn OH
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
16f
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
14
c081107dmma.0_002001r
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
Bu3Sn O
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
12a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
15
c081107dmma.0.001.001.1r.esp
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
Bu3Sn O
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
12a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
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9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
Bu3Sn O
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
12b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
17
a110404dmma377.002.001.1r.esp
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
Bu3Sn O
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
12b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
18
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
Chemical Shift (ppm)
Bu3Sn O
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
12d
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
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b080729dmma.5.001.001.1r.esp
200 192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
Bu3Sn O
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
12d
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
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10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
Chemical Shift (ppm)
Bu3Sn O
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
12e
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
21
a110331dmma317_1.002.001.1r.esp
200 192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
OBu3Sn
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
12e
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
22
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
Chemical Shift (ppm)
Bu3Sn O
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
12f
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
23
a110331dmma318_1.002.001.1r.esp
200 192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
Bu3Sn O
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
12f
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
24
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
Chemical Shift (ppm)
Bu3SnB
O
O
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
5
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
25
C0030595.001.001.1r.esp
144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
Bu3SnB
O
O
solvent: CDCl3 nucleus: 13C frequency: 100.61 MHz
5
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
26
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
B
O
OBu3Sn
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
6a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
27
c081110dmma.55.003.001.1r.esp
152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
B
O
OBu3Sn
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
6a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
28
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
Chemical Shift (ppm)
B
O
OBu3Sn
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
6b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
29
c080826dmma.3.001.001.1r.esp
152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
B
O
OBu3Sn
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
6b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
30
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
Chemical Shift (ppm)
Bu3SnB
O
O
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
6c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
31
c110217dmma.357.001.001.1r.esp
152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
Bu3SnB
O
O
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
6c
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
32
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
Chemical Shift (ppm)
Bu3SnB
O
O
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
6d
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
33
a111124dmma365_1.002.001.1r.esp
152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
Bu3SnB
O
O
solvent: CDCl3 nucleus: 13C
frequency: 75.48 MHz
6d
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
34
b100128dmma.125.002.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O O
OMe
TBS
solvent: CDCl3 nucleus: 1H
frequency: 300.132 MHz
43
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
35
b100128dmma.125.001.001.1r.esp
176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
O O
OMe
TBS
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
43
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
36
c100804dmma.257.002.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O OH
TBS
solvent: CDCl3 nucleus: 1H
frequency: 300.132 MHz
44
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
37
c100804dmma.257.001.001.1r.esp
105 100 95 90 85 80 75 70 65 60 55 50 45 40 35 30 25 20 15 10 5 0 -5
Chemical Shift (ppm)
O OH
TBS
solvent: CDCl3 nucleus: 13C
frequency: 75.48 MHz
44
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
38
md068.010.001.1r.esp
10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0 -0.5
Chemical Shift (ppm)
O O
TBS
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
19a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
39
200 192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
O O
TBS
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
19a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
40
b100128dmma.174.002.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O OH
TMS
TBS
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
21a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
41
b100128dmma.174.001.001.1r.esp
110 105 100 95 90 85 80 75 70 65 60 55 50 45 40 35 30 25 20 15 10 5 0 -5
Chemical Shift (ppm)
O OH
TMS
TBS
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
21a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
42
c091021dmma.152-R.001.esp
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O O
O
CF3
OMePh
TBS
TMS
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
45
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
43
c091021dmma.153-S.001.esp
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O O
O
CF3
PhOMe
TBS
TMS
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
46
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
44
c100804dmbe.06.002.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O OTBS
TMS
TBS
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
47
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
45
c100804dmbe.06.001.001.1r.esp
110 105 100 95 90 85 80 75 70 65 60 55 50 45 40 35 30 25 20 15 10 5 0 -5
Chemical Shift (ppm)
O OTBS
TMS
TBS
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
47
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
46
c100809dmbe.09.002.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O OTBS
H
TBS
solvent: CDCl3 nucleus: 1H
frequency: 300.132 MHz
48
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
47
c100809dmbe.09.001.001.1r.esp
90 85 80 75 70 65 60 55 50 45 40 35 30 25 20 15 10 5 0 -5
Chemical Shift (ppm)
O OTBS
H
TBS
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
48
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
48
a111114dmma180.001.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O OTBS
I
TBS
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
8a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
49
a111114dmma180.002.001.1r.esp
152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
O OTBS
I
TBS
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
8a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
50
d090828dmma.129 = 130im winscp.010.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
O O
OMeMeO
49
solvent: CDCl3 nucleus: 1H frequency: 500.130 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
51
d090828dmma.129 = 130im winscp.012.001.1r.esp
176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
O O
OMeMeO
solvent: CDCl3 nucleus: 13C
frequency: 125.76 MHz
49
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
52
b090901dmma.130II.001.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
O OH
MeO
50
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
53
b090901dmma.130II.003.001.1r.esp
160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
O OH
MeO
50
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
54
c090902dmma.131.001.001.1r.esp
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
O O
MeO
19b
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
55
c090902dmma.131.003.001.1r.esp
200 192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
O O
MeO
19b
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
56
c090907dmma.135-I.002.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O OH
MeO
TMS
21b
solvent: CDCl3 nucleus: 1H
frequency: 300.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
57
c090907dmma.135-I.001.001.1r.esp
160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
O OH
MeO
TMS
21b
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
58
b091006dmma.142_R.001.001.1r.esp
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O O
O
CF3
OMePh
MeO
TMS
51
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
59
b091006dmma.143_S.001.001.1r.esp
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O O
O
CF3
PhOMe
MeO
TMS
52
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
60
b091210dmma.164.002.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O OTBS
MeO
TMS
53
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
61
b091210dmma.164.001.001.1r.esp
160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
O OTBS
MeO
TMS
53
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
62
b091209dmma.165.001.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O OTBS
MeO
H
54
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
63
b091209dmma.165.003.001.1r.esp
160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
O OTBS
MeO
H
54
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
64
a111116dmma180_I.001.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O OTBS
IMeO
8b
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
65
a111116dmma180_I.002.001.1r.esp
160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
O OTBS
IMeO
8b
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
66
a120210dmma314_3.001.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
O OH
MeO
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
22
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
67
a120210dmma314_3.002.001.1r.esp
160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0
Chemical Shift (ppm)
O OH
MeO
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
22
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
68
c110117dmma.325_R.001.001.1r.esp
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
O O
O
PhOMe
CF3
MeO
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
55
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
69
c110117dmma.326_S.001.001.1r.esp
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
O O
O
CF3
PhOMe
MeO
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
56
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
70
a110805dmma438.001.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O OTBS
MeO
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
57
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
71
a110805dmma438.002.001.1r.esp
160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0
Chemical Shift (ppm)
O OTBS
MeO
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
57
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
72
a110808dmma444.001.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O O
SnBu3MeO
TBS
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
58
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
73
a110808dmma444.002.001.1r.esp
152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0
Chemical Shift (ppm)
O O
SnBu3MeO
TBS
solvent: CDCl3 nucleus: 13C
frequency: 75.48 MHz
58
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
74
a111115dmma445.001.001.1r.esp
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0 -0.5
Chemical Shift (ppm)
O O
IMeO
TBS
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
7
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
75
a111115dmma445.002.001.1r.esp
160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0
Chemical Shift (ppm)
O O
IMeO
TBS
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
7
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
76
b081119dmma.51_001001r
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5
Chemical Shift (ppm)
OMe
O
O
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
24
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
77
b081119dmma.51_002001r
200 192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24
Chemical Shift (ppm)
OMe
O
O
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
24
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
78
b090514dmae.001.001.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0
Chemical Shift (ppm)
OMe
O
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
59
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
79
b090514dmae.001.002.001.1r.esp
176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24
Chemical Shift (ppm)
OMe
O
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
59
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
80
c080926dmma.9_002001r
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5
Chemical Shift (ppm)
OMe
O
O
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
26
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
81
c080926dmma.9_001001r
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24
Chemical Shift (ppm)
OMe
O
O
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
26
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
82
c090616dmae.09.002.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0
Chemical Shift (ppm)
OMe
O
OH
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
27
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
83
d081024dmnb.25_012001r
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24
Chemical Shift (ppm)
OMe
O
OH
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
27
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
84
c090309dmma.R.001.001.1r.esp
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5
Chemical Shift (ppm)
OMe
O
O O
MeOCF3
Ph
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
60
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
85
c090309dmma.S.001.001.1r.esp
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0
Chemical Shift (ppm)
OMe
O
O O
F3C OMePh
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
61
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
86
c090616dmae.10.001.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
OMe
O
OTBS
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
62
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
87
c090616dmae.10.002.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
OMe
O
OTBS
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
62
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
88
c090616dmae.12.002.001.1r.esp
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
OMe
O
OTBS
O
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
63
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
89
c081022dmnb.26_003001r
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
OMe
O
OTBS
O
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
63
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
90
AE015_me.010.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
OMe
O
OTBS
I
10
E/Z = 7:1
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
91
c081111dmma.57.003.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0
Chemical Shift (ppm)
OMe
O
OTBS
I
10
E/Z = 7:1
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
92
c081112dmma.58.001.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
OMe
O
OH
I
solvent: CDCl3 nucleus: 1H
frequency: 300.132 MHz
28
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
93
c081112dmma.58.003.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
OMe
O
OH
I
solvent: CDCl3 nucleus: 13C
frequency: 75.48 MHz
28
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
94
c101006dmma.JS01.002.001.1r.esp
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5
Chemical Shift (ppm)
OEt
O
O
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
64
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
95
c100909dmma.266.001.001.1r.esp
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
OEt
O
O
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
64
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
96
c101008dmma.JS02.002.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5
Chemical Shift (ppm)
O
OEt
OH
solvent: CDCl3 nucleus: 1H
frequency: 300.132 MHz
32
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
97
c101008dmma.JS02.001.001.1r.esp
176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16
Chemical Shift (ppm)
O
OEt
OH
solvent: CDCl3 nucleus: 13C
frequency: 75.48 MHz
32
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
98
c101025dmma.JS06.001.001.1r.esp
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
O
OEt
OO
PhCF3
OCH3
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
65
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
99
c101025dmma.JS09.001.001.1r.esp
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
O
OEt
OO
PhOCH3
CF3
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
66
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
100
c101011dmma.JS03.002.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O
OEt
OTBS
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
67
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
101
c101011dmma.JS03.004.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
O
OEt
OTBS
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
67
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
102
me_majs04.60010.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O
OH
OTBS
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
68
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
103
c101011dmma.JS04.004.001.1r.esp
176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
O
OH
OTBS
solvent: CDCl3 nucleus: 13C
frequency: 75.48 MHz
68
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
104
c101026dmma.JS08.002.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O
OMe
OTBS
solvent: CDCl3 nucleus: 1H
frequency: 300.132 MHz
33
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
105
c101026dmma.JS08.001.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0
Chemical Shift (ppm)
O
OMe
OTBS
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
33
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
106
c101025dmma.JS13.002.001.1r.esp
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O
OMe
OTBS
O
solvent: CDCl3 nucleus: 1H
frequency: 300.132 MHz
69
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
107
c101025dmma.JS13.001.001.1r.esp
192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
O
OMe
OTBS
O
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
69
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
108
a111019dmma474.001.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
I
OTBS
OMe
O
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
18 9
E/Z = 8:1
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
109
a111019dmma474.002.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
I
OTBS
OMe
O
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
18 9
E/Z = 8:1
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
110
me_ab016II.60010.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
OTBS
O
OMeBO
O
37a
solvent: CDCl3 nucleus: 1H frequency: 600.130 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
111
c090710dmma.108.001.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
OTBS
O
OMeBO
O
37a
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
112
c090710dmma.109.002.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
OTBS
O
OMeBO
O
37b
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
113
c090710dmma.109.001.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0
Chemical Shift (ppm)
OTBS
O
OMeBO
O
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
37b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
114
me_ab017.60010.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
OTBS
O
OMe
OTBSO
TBS
38a
solvent: CDCl3 nucleus: 1H frequency: 600.130 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
115
me_ab017.60011.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
OTBS
O
OMe
OTBSO
TBS
solvent: CDCl3 nucleus: 13C frequency: 150.90 MHz
38a
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
116
c100331dmma.205.001.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
OTBS
O
OMe
O OTBS
TBS
38b
solvent: CDCl3 nucleus: 1H frequency: 300.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
117
c100331dmma.205.002.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
OTBS
O
OMe
O OTBS
TBS
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
38b
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
118
d100331dmab.018.001.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
OTBS
O
OMe
OTBSO
OMe
39a
solvent: CDCl3 nucleus: 1H frequency: 500.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
119
d100331dmab.018.002.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
OTBS
O
OMe
OTBSO
OMe
39a
solvent: CDCl3 nucleus: 13C frequency: 125.76 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
120
me_ma204.60010.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O OTBS OTBS
OMe
O
OMe
39b
solvent: CDCl3 nucleus: 1H frequency: 600.130 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
121
me_ma204.60011.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
O OTBS OTBS
OMe
O
OMe
39b
solvent: CDCl3 nucleus: 13C frequency: 150.90 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
122
d110923dmma.467.002.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
Chemical Shift (ppm)
OH
O
OMe
OHOH
4a
solvent: CDCl3 nucleus: 1H frequency: 500.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
123
d110923dmma.467.001.001.1r.esp
176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8
Chemical Shift (ppm)
OH
O
OMe
OHOH
4a
solvent: CDCl3 nucleus: 13C frequency: 125.76 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
124
d110923dmma.468.002.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5
Chemical Shift (ppm)
OH OH OH
OMe
O
4b
solvent: CDCl3 nucleus: 1H
frequency: 500.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
125
d110923dmma.468.001.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16
Chemical Shift (ppm)
OH OH OH
OMe
O
4b
solvent: CDCl3 nucleus: 13C frequency: 125.76 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
126
me_ma460.60010.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
OH
O
OMe
OHO
OMe
4c
solvent: CDCl3 nucleus: 1H frequency: 399.982 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
127
me_ma460.60016.001.1r.esp
176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0
Chemical Shift (ppm)
OH
O
OMe
OHO
OMe
4c
solvent: CDCl3 nucleus: 13C frequency: 150.90 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
128
me_ma207.60010.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
O OH OH
OMe
O
OMe
4d
solvent: CDCl3 nucleus: 1H frequency: 300.13 2MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
129
me_ma305.60012.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16
Chemical Shift (ppm)
O OH OH
OMe
O
OMe
4d
solvent: CDCl3 nucleus: 13C frequency: 150.90 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
130
a110505dmma395.001.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
OMe
O
OTBS
B
O
O
40
solvent: CDCl3 nucleus: 1H
frequency: 300.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
131
a110505dmma395.002.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
OMe
O
OTBS
B
O
O
40
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
132
me_ma419.60010.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
BO
O
OOPMB TBS
42
solvent: CDCl3 nucleus: 1H
frequency: 300.132 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
133
me_ma419.60012.001.1r.esp
160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
BO
O
OOPMB TBS
42
solvent: CDCl3 nucleus: 13C frequency: 75.48 MHz
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
134
me_ma463.60010.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0
Chemical Shift (ppm)
O
O
OMe
OO
TBS TBS
OMe
solvent: CDCl3 nucleus: 1H frequency: 600.130 MHz
41
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
135
me_ma463.60012.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0 -8
Chemical Shift (ppm)
O
O
OMe
OO
TBS TBS
OMe
solvent: CDCl3 nucleus: 13C frequency: 150.90 MHz
41
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
136
me_ma476.60010.001.1r.esp
7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0
Chemical Shift (ppm)
OH
O
OMe
OHO
OMe
solvent: CDCl3 nucleus: 1H
frequency: 600.130 MHz
3
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
137
me_ma476.60011.001.1r.esp
168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16
Chemical Shift (ppm)
OH
O
OMe
OHO
OMe
solvent: CDCl3 nucleus: 13C frequency: 150.90 MHz
3
Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012
