通过铟介导的烯丙基化反应不对称合成埃坡菌素A和B。

Asymmetric syntheses of epohelmins A and B by In-mediated allylation.

作者信息

Liu Yi-Wen, Han Pan, Zhou Wen, Mao Zhuo-Ya, Si Chang-Mei, Wei Bang-Guo

机构信息

Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, China.

出版信息

Org Biomol Chem. 2016 Dec 7;14(45):10714-10722. doi: 10.1039/c6ob02212j. Epub 2016 Nov 2.

DOI:10.1039/c6ob02212j

PMID:27805230

Abstract

A diastereoselective new approach for the synthesis of trans-4-hydroxy-5-allyl-2-pyrrolidinone 9 has been developed through In-mediated allylation of α-chiral aldimine 8 with allyl bromide. The stereochemistry at the C-2 stereogenic center of 9 was controlled by both the α-OTBS substitution and the sulfinamide moiety. The utility of this asymmetric allylation is demonstrated by the asymmetric syntheses of epohelmins A (4) and B (10).

摘要

通过铟介导的α-手性醛亚胺8与烯丙基溴的烯丙基化反应，开发了一种非对映选择性合成反式-4-羟基-5-烯丙基-2-吡咯烷酮9的新方法。9的C-2立体中心的立体化学由α-OTBS取代基和亚磺酰胺部分共同控制。通过埃坡菌素A（4）和B（10）的不对称合成证明了这种不对称烯丙基化反应的实用性。