Synthesis of (±)-anatoxin-a and analogues

被引：44

作者：

Parsons, PJ ^{[1
]}

Camp, NP ^{[1
]}

Edwards, N ^{[1
]}

Sumoreeah, LR ^{[1
]}

机构：

[1] Univ Sussex, Chem Labs, Sch Chem Phys & Environm Sci, Brighton BN1 9QJ, E Sussex, England

来源：

TETRAHEDRON | 2000年 / 56卷 / 02期

关键词：

(+/-)-anatoxin-alpha; beta-lactam; transannular cyclisation;

D O I：

10.1016/S0040-4020(99)00909-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and highly efficient synthesis of the potent nicotinic acetylcholine receptor agonist, anatoxin-a and its analogues is described, which uses a beta-lactam ring opening-transannular cyclisation sequence to set up the bridged bicyclic framework of the natural product. The synthesis involves a cycloaddition of chlorosulfonyl isocyanate with cyclooctadiene followed by Boc protection of the resulting beta-lactam. Reaction of the beta-lactam with a variety of nucleophiles, followed by selenium-mediated cyclisation and oxidation gave the skeleton of anatoxin-a bearing various sidechains. The approach offers a flexible entry to useful quantities of anatoxin-a and its analogues. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：309 / 315

页数：7

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