Medium ring stereocontrol in the functionalisation of eight-membered lactones

被引：14

作者：

Anderson, EA

Holmes, AB

Collins, I

机构：

[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England

[2] Merck Sharp & Dohme Res Labs, Neurosci Res Ctr, Harlow CM20 2QR, Essex, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 01期

基金：

英国工程与自然科学研究理事会;

关键词：

asymmetric induction; lactones; stereocontrol; oxygenation;

D O I：

10.1016/S0040-4039(99)01988-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Medium ring lactones with up to three substituents have been prepared as single diastereoisomers via Claisen rearrangement. Application of medium ring stereocontrol to a gamma,delta-unsaturated eight-membered ring lactone prepared by this route enabled the overall diastereoselective functionalisation of all but one of the ring positions. A comparison of the ring-induced selectivity was made with that of the corresponding acyclic hydroxy ester which exhibited an overall reversal of stereoselectivity. This methodology provides access to highly substituted polyketide fragments. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：117 / 121

页数：5

共 15 条

[1] MAJOR IMPROVEMENT IN OSMIUM CATALYZED VICINAL HYDROXYLATION OF OLEFINS BY TERT-BUTYL HYDROPEROXIDE [J].