邻位锂化芳基环氧乙烷与α,β-不饱和丙二酸酯的迈克尔加成反应：四氢茚并呋喃酮的合成

Michael addition of ortho-lithiated aryloxiranes to alpha,beta-unsaturated malonates: synthesis of tetrahydroindenofuranones.

作者信息

Salomone Antonio, Capriati Vito, Florio Saverio, Luisi Renzo

机构信息

Dipartimento Farmaco-Chimico, Università di Bari, Consorzio Interuniversitario Nazionale Metodologie e Processi Innovativi di Sintesi, Via E.Orabona 4, I-70125 Bari, Italy.

出版信息

Org Lett. 2008 May 15;10(10):1947-50. doi: 10.1021/ol800437s. Epub 2008 Apr 19.

DOI:10.1021/ol800437s

PMID:18422323

Abstract

A short and efficient synthesis of tetrahydroindenofuranones based on the Michael addition of ortho-lithiated aryloxiranes to alkylidene malonates followed by the nucleophilic oxirane ring-opening and subsequent lactonization is described. The methodology has been applied to the synthesis of a structural analogue of epipodophyllotoxins.

摘要

描述了一种基于邻位锂化芳基环氧乙烷与亚烷基丙二酸酯的迈克尔加成反应，随后进行亲核环氧乙烷开环和后续内酯化反应的短而高效的四氢茚并呋喃酮合成方法。该方法已应用于表鬼臼毒素结构类似物的合成。