(+)-达瓦酮的简洁仿生全合成。

A concise, biomimetic total synthesis of (+)-davanone.

作者信息

Morrison Karen C, Litz Jonathan P, Scherpelz Kathryn P, Dossa Paul D, Vosburg David A

机构信息

Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, California 91711, USA.

出版信息

Org Lett. 2009 May 21;11(10):2217-8. doi: 10.1021/ol900697w.

DOI:10.1021/ol900697w

PMID:19366191

Abstract

A concise, biomimetic synthesis of the antifungal and antispasmodic natural product (+)-davanone is described. The key stereoselective reactions are a Sharpless asymmetric epoxidation, a thiazolium-catalyzed esterification, and a palladium-mediated cyclization. All carbons are derived from isoprene units and no protecting groups are used, permitting an atom- and redox-economical synthesis.

摘要

本文描述了抗真菌和抗痉挛天然产物（+）-达瓦酮的简洁仿生合成方法。关键的立体选择性反应包括夏普莱斯不对称环氧化反应、噻唑鎓催化的酯化反应和钯介导的环化反应。所有碳原子均来源于异戊二烯单元，且未使用保护基，从而实现了原子经济性和氧化还原经济性的合成。