Total synthesis of (-)-salicylihalamide A and related congeners

被引：50

作者：

Smith, AB ^{[1
]}

Zheng, JY

机构：

[1] Univ Penn, Dept Chem, Res Struct Matter Lab, Philadelphia, PA 19104 USA

[2] Univ Penn, Monell Chem Senses Ctr, Philadelphia, PA 19104 USA

来源：

TETRAHEDRON | 2002年 / 58卷 / 32期

基金：

美国国家卫生研究院;

关键词：

salicylihalamide; total synthesis; macrocycles; metathesis; Curtius rearrangement;

D O I：

10.1016/S0040-4020(02)00657-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise, highly efficient total synthesis of (-)-salicylihalamide A (1), a novel marine sponge metabolite, has been achieved. Key features of the synthetic strategy include a highly E-selective ring-closing metathesis to construct the 12-membered salicylihalamide A macrocycle and a practical method for installation of the labile ene-hepta-(Z,Z)-dienamide side chain involving N-acylation of enecabarmate, 5, the latter derived from the corresponding a, P-unsaturated carboxylic acid 28 via acyl azide formation and thermal Curtius rearrangement. Two structurally simplified analogs (3 and 4) were also prepared which displayed significant, but attenuated cell growth inhibitory activity against several human tumor cell lines. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：6455 / 6471

页数：17

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