First total syntheses of dihydroflustramine C and flustramine E, alkaloids from the marine bryozoan Flustra foliacea

被引：32

作者：

Morales-Ríos, MS ^{[1
]}

Suárez-Castillo, OR ^{[1
]}

Joseph-Nathan, P ^{[1
]}

机构：

[1] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico

来源：

TETRAHEDRON | 2002年 / 58卷 / 08期

关键词：

dihydroflustramine C; flustramine E; indole alkaloids; total synthesis;

D O I：

10.1016/S0040-4020(02)00011-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a simple and practical method for providing the common tricyclic skeleton of physostigmine type alkaloids, and demonstrated its utility for indole alkaloid synthesis. Thus, we achieved the first total syntheses of (+/-)-dihydroflustramine C and (+/-)-flustramine E, as well as the total syntheses of their debromoanalogues from the corresponding 2-hydroxyindolenines in five steps with 31, 27, 39 and 23% overall yields, respectively. The structures of some intermediates were confirmed by single crystal X-ray diffraction analyses. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：1479 / 1484

页数：6

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