The telescoped intramolecular Michael/olefination (TIMO) approach to α-alkylidene-γ-butyrolactones:: Synthesis of (+)-paeonilactone B

被引：66

作者：

Edwards, Michael G. ^{[1
]}

Kenworthy, Martin N. ^{[1
]}

Kitson, Russell R. A. ^{[1
]}

Scott, Mark S. ^{[1
]}

Taylor, Richard J. K. ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 10期

基金：

英国工程与自然科学研究理事会;

关键词：

alpha-methylene lactones; Michael addition; olefination; phosphonates; tandem reactions;

D O I：

10.1002/anie.200705329

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Scoping out TIMO: A telescoped intramolecular Michael addition/proton transfer/ Horner-Wadsworth-Emmons olefination sequence was developed to provide rapid access to α-alkylidene-γ- butyrolactones (see scheme). The method was applied to prepare a range of tetrahydrobenzofuran-2,5-diones and related systems, and it was utilized in a short synthesis of enantiomerically pure (+)-paeonilactone B. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1935 / 1937

页数：3

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