Chiral vicinal diols as platforms for separable diastereomers in Johnson-Claisen rearrangement: a new short route to (-)-nor-canadensolide, (-)-canadensolide and (-)-sporothriolide

被引：19

作者：

Fernandes, Rodney A. ^{[1
]}

Ingle, Arun B. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 10期

关键词：

Asymmetric synthesis; Chiral vicinal diols; Johnson-Claisen rearrangement; Nor-canadensolide; Canadensolide; Sporothriolide; ENANTIOSELECTIVE SYNTHESIS; FORMAL SYNTHESIS; STEREOSELECTIVE SYNTHESIS; ALLYLIC ALCOHOLS; GAMMA-LACTONES; SPOROTHRIOLIDE; 4-EPI-ETHISOLIDE; LACTONIZATION; CANADENSOLIDE; ACID;

D O I：

10.1016/j.tetlet.2008.12.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral vicinal diols prepared by asymmetric dihydroxylation in high enantioselectivities provide an excellent platform for separable diastereomers in the Johnson-Claisen rearrangement. The separated syn-diastereomers were converted into the advanced gamma-(lactone-lactol) intermediates (in six steps, 26-27% overall yields) for the synthesis of (-)-nor-canadensoiide, (-)-canadensolide and (-)-sporothriolide. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：1122 / 1124

页数：3

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