Synthesis of the C1-C26 northern portion of azaspiracid-1: Kinetic versus thermodynamic control of the formation of the bis-spiroketal

被引：35

作者：

Zhou, XT ^{[1
]}

Carter, RG ^{[1
]}

机构：

[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 11期

关键词：

azaspiracid-1; fused-ring systems; natural products; spiro compounds;

D O I：

10.1002/anie.200503733

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

North-South divide: An efficient synthesis of the entire C1-C26 (northern) portion of azaspiracid-1 is disclosed (see picture). Key transformations include the formation of a bis-spiroketal, the oxidation of a sulfone at C10 to form a β,γ-unsaturated ketone, a tandem Wadsworth-Emmons/hetero-Michael addition to construct ring D, and the highly selective hydroxylation at C20. (Chemical Equation Presented) © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1787 / 1790

页数：4