Total Synthesis of ( ­­¶ )-Enigmazole - .Background • Marine...

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Transcript of Total Synthesis of ( ­­¶ )-Enigmazole - .Background • Marine...

  • Total Synthesis of ( -- )-Enigmazole A1

    Presented by: Grace HubbellCEM 852

    4/14/20181. J. Am. Chem. Soc. 2015, 137, 15426-15429.

  • Background

    Marine macrolide isolated from the marine sponge Cinachyrella enigmatica in 2006.2Cytotoxic towards NCI human

    tumor cell lines.3First total synthesis achieved

    in 2010 by Molinski.4

    2. Oku, N.; Gustafson, K.R.; Fuller, R.W.; Wilson, J.A.; Panell, L.K.; McMahon, J.B. Symposium on the Chemistry of Natural Products 2006, 73. 3. Oku, N.; Takada, K.; Fuller, R.W.; ;Wilson, J.A.; Peach, M.L.; Panell, L.K.; McMachon, J.B.; Gustafson, K.R. J. Am. Chem. Soc. 2010, 132, 10278.4. Skepper, C.K.; Quach, T.; Molinski, T.F. J. Am. Chem Soc. 2010, 132, 10286.

  • Retrosynthe@c Approach & Key Reac@ons

  • Prepara@on of Epoxide()-7

    I. Chem. Eur. J. 2014, 20(30) 9336.II. Chem. Eur. J. 2012, 18(52) 16868.

  • Prepara@on of Dithiane (+)-6

  • Construc@on of EasternHemisphere(+)-5

  • Construc@on of EasternHemisphere(+)-5

  • Construc@on of WesternHemisphere()-4

  • Construc@on of WesternHemisphere()-4

  • Petasis-Ferrier Union/Rearrangement

  • Petassis-Ferrier Union/Rearrangement

  • Macrolactone (+)-33Forma@on

  • Phosphoric Acid Forma@on