Synthesis of (±)-solanapyrones A and B

被引：18

作者：

Lygo, B ^{[1
]}

Bhatia, M

Cooke, JWB

Hirst, DJ

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] Univ Salford, Dept Chem, Salford M5 4WT, Lancs, England

[3] GlaxoSmithKline, Stevenage SG1 2NY, Herts, England

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 12期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(03)00288-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper we report the development of a stereoselective IMDA approach to the phytotoxic polyketides (+/-)-solanapyrones A and B. The stereoselectivity of the key IMDA cycloaddition was optimized by investigating a range of 2,8,10-dodecatrienoic acid derivatives. This established that use of the Weinreb amide led to the desired exo-selectivity and also facilitated construction of the pyrone moiety. A novel approach to the installation of the C-3 formyl group in solanapyrone A is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.

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页码：2529 / 2532

页数：4

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