New synthetic approach to pyrroloiminoquinone marine alkaloids. Total synthesis of makaluvamines A, D, I, and K

被引：53

作者：

Iwao, M

Motoi, O

Fukuda, T

Ishibashi, F

机构：

[1] Nagasaki Univ, Fac Engn, Dept Appl Chem, Nagasaki 8528521, Japan

[2] Nagasaki Univ, Fac Fisheries, Dept Marine Biochem, Nagasaki 8528521, Japan

来源：

TETRAHEDRON | 1998年 / 54卷 / 31期

关键词：

D O I：

10.1016/S0040-4020(98)00543-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new entry into pyrroloiminoquinone marine alkaloids, makaluvamines, has been developed. The key 1,3,4,5-tetrahydropyrrolo [4,3,2-de]quinoline intermediates 11 and 18 were prepared by aryne-mediated cyclization of the 4-chloro-6-methoxytryptamine derivatives 10 and 17, respectively. The requisite substituents at the indole 4- and 3-positions of 10 and 17 were efficiently assembled by sequential use of directed lithiation of 1-triisopropylsilyl-6-methoxygramine (6) and fluoride ion-induced elimination-addition of the methiodide of 4-chloro-1-triisopropylsilyl-6-methoxygramine (7) as key reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：8999 / 9010

页数：12

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