A simple and practical approach to the synthesis of the marine sponge pigment fascaplysin and related compounds

被引：55

作者：

Radchenko, OS ^{[1
]}

Novikov, VL ^{[1
]}

Elyakov, GB ^{[1
]}

机构：

[1] RUSSIAN ACAD SCI,PACIFIC INST BIOORGAN CHEM,FAR E DIV,VLADIVOSTOK 690022,RUSSIA

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(97)01167-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fascaplysin (1) under bar an antimicrobial and cytotoxic red pigment of the marine sponge Fascaplysinopsis sp. has been synthesized in five steps from tryptamine (2) under bar in 44% overall yield. The key steps in the synthesis are: (a) dehydrogenation of the dihydro-beta-carboline intermediate (4) under bar simultaneously with its benzylic oxidation on treatment with MnO2 and (b) the thermal cyclization of the resulting beta-carboline (7) under bar into a quaternary salt 8. Similarly, indoloisoquinolines <(15)under bar> and <(16)under bar> the tetracyclic analogues of (1) under bar were prepared in six: steps from alpha-amino ketone (9) under bar in 59 and 55% overall yields, respectively. (C) 1997 Elsevier Science Ltd.

引用

页码：5339 / 5342

页数：4

共 6 条

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