阴离子接力化学的拓展。柳珊瑚倍半萜的合成。

Anion relay chemistry extended. Synthesis of a gorgonian sesquiterpene.

作者信息

Smith Amos B, Kim Dae-Shik, Xian Ming

机构信息

Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.

出版信息

Org Lett. 2007 Aug 16;9(17):3307-9. doi: 10.1021/ol071281j. Epub 2007 Jul 18.

DOI:10.1021/ol071281j

PMID:17637030

Abstract

Extension of anion relay chemistry (ARC) beyond the area of dithianes has been achieved by the design of two effective ARC linchpins capable of three- and four-component couplings. To showcase the ARC tactic in natural product synthesis, a cytotoxic gorgonian linear sesquiterpene was constructed, and the absolute configuration assigned via the Kakisawa/Mosher method. The synthesis proceeded in five steps with an overall yield of 22%.

摘要

通过设计两种能够进行三组分和四组分偶联的有效阴离子中继化学（ARC）关键部件，实现了阴离子中继化学（ARC）在二噻烷领域之外的扩展。为了展示ARC策略在天然产物合成中的应用，构建了一种具有细胞毒性的柳珊瑚线性倍半萜，并通过Kakisawa/Mosher方法确定了其绝对构型。该合成过程分五步进行，总收率为22%。