Stereocontrol of 5,5-Spiroketals in the Synthesis of Cephalosporolide H Epimers

被引：53

作者：

Tlais, Sami F. ^{[1
]}

Dudley, Gregory B. ^{[1
]}

机构：

[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 20期

基金：

美国国家科学基金会;

关键词：

MARINE-DERIVED FUNGUS; ASYMMETRIC-SYNTHESIS; CD-SPIROKETAL; REDUCTION; SPIROACETALS; DERIVATIVES; EPOXIDES; LACTONES; AB;

D O I：

10.1021/ol102201z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A blueprint for controlling the stereochemistry of oxygenated 5,5-spiroketals using chelation effects is provided. Chelation specifically of zinc salts (other protic and Lewis acids were less effective) between the spiroketal oxygen and an appropriately positioned alcohol group overrides normal biases in the preparation of 5,5-spiroketals, as illustrated by the stereocontrolled synthesis of epimeric cephalosporolide H isomers. This study provides new and valuable information for prescribing the chirality of the stereogenic core of 5,5-spiroketals.

引用

页码：4698 / 4701

页数：4

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