志摩内酯的仿生合成

Biomimetic synthesis of the shimalactones.

作者信息

Sofiyev Vladimir, Navarro Gabriel, Trauner Dirk

机构信息

Department of Chemistry, University of California Berkeley, Berkeley, California 94720-1460, USA.

出版信息

Org Lett. 2008 Jan 3;10(1):149-52. doi: 10.1021/ol702806v. Epub 2007 Dec 12.

DOI:10.1021/ol702806v

PMID:18072785

Abstract

A biomimetic synthesis of shimalactone A and B is described. Its key features are an unprecedented acid-catalyzed cyclization of a dienyl beta-ketolactone and a Stille coupling/8pi-6pi electrocyclization cascade to create the oxabicyclo[2.2.1]heptane and bicyclo[4.2.0]octadiene, respectively. The synthesis is convergent and void of protecting groups.

摘要

本文描述了喜玛内酯A和B的仿生合成。其关键特征包括前所未有的酸催化二烯基β-酮内酯环化反应，以及通过Stille偶联/8π-6π电环化串联反应分别构建氧杂双环[2.2.1]庚烷和双环[4.2.0]辛二烯。该合成方法具有汇聚性且无需保护基团。