Chemistry of Renieramycins. Part 4. Synthesis of a Simple Natural Marine Product,...

2004 Other natural products Other natural products U 0800 Chemistry of Renieramycins. Part 4. Synthesis of a Simple Natural Marine Prod- uct, 6-Hydroxy-7-methoxyisoquinolinemethanol. — Recently, mimosamycin and the title compound (X) were isolated from the marine sponge Haliclona sp. Because the biosynthetic pathway of this natural product may be different from those of the marine sponges renierone and its derivatives, its structure is synthesized by a five-step synthesis from known compound (I). According to a modified Pomeranz—Fritsch isoquino- line synthesis, (I) is obtained from vanillin in five steps with 65% overall yield. With regard to the practical synthesis of (X), the isopropyl group is chosen as the appropriate protecting group for the phenolic function. Since direct conversion of (VI) into the final compound (X) fails, the reaction sequence (VI)→(VIII)→(IX)→(X) succeeds in pre- paring the structure reported for the natural product. — (SAITO*, N.; TANAKA, C.; SATOMI, T.; OYAMA, C.; KUBO, A.; Chem. Pharm. Bull. 52 (2004) 2, 282-286; Meiji Pharm. Univ., Kiyose, Tokyo 204, Japan; Eng.) — H. Hoennerscheid 30- 201

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Transcript of Chemistry of Renieramycins. Part 4. Synthesis of a Simple Natural Marine Product,...

Page 1: Chemistry of Renieramycins. Part 4. Synthesis of a Simple Natural Marine Product, 6-Hydroxy-7-methoxyisoquinolinemethanol.

2004 Other natural products

200430.fm Page 209 Thursday, July 1, 2004 10:50 AM

Other natural productsU 0800 Chemistry of Renieramycins. Part 4. Synthesis of a Simple Natural Marine Prod-

uct, 6-Hydroxy-7-methoxyisoquinolinemethanol. — Recently, mimosamycin and the title compound (X) were isolated from the marine sponge Haliclona sp. Because the biosynthetic pathway of this natural product may be different from those of the marine sponges renierone and its derivatives, its structure is synthesized by a five-step synthe-sis from known compound (I). According to a modified Pomeranz—Fritsch isoquino-line synthesis, (I) is obtained from vanillin in five steps with 65% overall yield. With regard to the practical synthesis of (X), the isopropyl group is chosen as the appropriate protecting group for the phenolic function. Since direct conversion of (VI) into the final compound (X) fails, the reaction sequence (VI)→(VIII)→(IX)→(X) succeeds in pre-paring the structure reported for the natural product. — (SAITO*, N.; TANAKA, C.; SATOMI, T.; OYAMA, C.; KUBO, A.; Chem. Pharm. Bull. 52 (2004) 2, 282-286; Meiji Pharm. Univ., Kiyose, Tokyo 204, Japan; Eng.) — H. Hoennerscheid

30- 201