The synthesis of a natural product family: from debromoisolaurinterol to the aplysins

被引：49

作者：

Harrowven, DC ^{[1
]}

Lucas, MC

Howes, PD

机构：

[1] Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England

[2] Glaxo Wellcome Res & Dev Ltd, Med Res Ctr, Med Chem 2, Stevenage SG1 2NY, Herts, England

来源：

TETRAHEDRON | 2001年 / 57卷 / 04期

基金：

英国工程与自然科学研究理事会;

关键词：

terpenes and terpenoids; natural products; radicals and radical reactions; cyclisations; oxygen heterocycles;

D O I：

10.1016/S0040-4020(00)01055-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total syntheses of (+/-)-aplysin 1, (+/-)-debromoaplysin 2, (+/-)-isoaplysin 3, (+/-)-aplysinol 4, (+/-)-debromoaplysinol 5, (+/-)-aplysinal 6, (+/-)-isolaurinterol 7 and (+/-)-debromoisolaurinterol 8 are described. Key features are a diastereoselective, sulfur mediated radical cyclisation of diene 12 to give 35; a new radical to polar crossover sequence mediated by Bu3Sn that transforms diene 12 into (+/-)-debromoisolaurinterol 8; and a series of biomimetic cyclisation and oxidation reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：791 / 804

页数：14

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