Dual Macrolactonization/Pyran-Hemiketal Formation via Acylketenes: Applications to the Synthesis of (-)-Callipeltoside A and a Lyngbyaloside B Model System

被引：31

作者：

Hoye, Thomas R. ^{[1
]}

Danielson, Michael E. ^{[1
]}

May, Aaron E. ^{[1
]}

Zhao, Hongyu ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 50期

基金：

美国国家卫生研究院;

关键词：

acylketenes; alcohols; concerted addition; lactones; regioselectivity;

D O I：

10.1002/anie.200804049

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two for one: Thermal generation of acylketenes in diol-containing substrates results in the title transformation. This transformation expands the scope of acylketene macrolactonizations and their application to the synthesis of complex macrolides. Triol and tetraol substrates have also been cyclized in highly regioselective fashion. Additionally, the challenging macrolactonization of a tertiary alcohol was achieved. (Chemical Equation Presented). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：9743 / 9746

页数：4

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