通过分子内 Mukaiyama 羟醛缩合反应合成瓜纳卡斯特烯 A 的 [5-7-6] 三环核心。

Synthesis of the [5-7-6] tricyclic core of guanacastepene A via an intramolecular Mukaiyama aldol reaction.

作者信息

Du Xiaohui, Chu Hiufung V, Kwon Ohyun

机构信息

Department of Chemistry & Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, USA.

出版信息

Org Lett. 2003 May 29;5(11):1923-6. doi: 10.1021/ol0344873.

DOI:10.1021/ol0344873

PMID:12762687

Abstract

[reaction: see text] A synthesis of the tricyclic [5-7-6] skeleton of guanacastepene A is described. The six-membered ring of guanacastepene A was constructed by a Diels-Alder reaction. After several functional group transformations, it was coupled to beta-iodocyclopentenone. Lithium dimethylcuprate conjugate addition followed by an intramolecular Mukaiyama aldol reaction furnished the desired [5-7-6] tricyclic ring system.

摘要

[反应：见正文] 描述了番荔枝烯A的三环[5-7-6]骨架的合成。番荔枝烯A的六元环通过狄尔斯-阿尔德反应构建。经过几次官能团转化后，它与β-碘环戊烯酮偶联。二甲基铜锂共轭加成，随后进行分子内 Mukaiyama 羟醛反应，得到了所需的[5-7-6]三环体系。