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
收藏
页码：1787 / 1790
页数：4
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