通过分子间环丙烷化反应合成手性3-取代六氢吡咯并吲哚啉

Synthesis of chiral 3-substituted hexahydropyrroloindoline via intermolecular cyclopropanation.

作者信息

Song Hao, Yang Jun, Chen Wei, Qin Yong

机构信息

Department of Chemistry of Medicinal Natural Products and Key Laboratory of Drug Targeting, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. China.

出版信息

Org Lett. 2006 Dec 21;8(26):6011-4. doi: 10.1021/ol062489s.

DOI:10.1021/ol062489s

PMID:17165917

Abstract

[Structure: see text] A new and efficient synthetic route to chiral 3-substituted hexahydropyrroloindoline 18 possessing absolute configurations in accordance with indole alkaloids has been developed from readily available L-tryptophan. The key step relies on the one-pot cascade reaction of oxazolidinone 17 with diazoester, which proceeds through intermolecular cyclopropanation, ring opening, and cyclization.

摘要

[结构：见正文] 已从容易获得的L-色氨酸开发出一种新的、高效的合成路线，用于制备具有与吲哚生物碱一致的绝对构型的手性3-取代六氢吡咯并吲哚啉18。关键步骤依赖于恶唑烷酮17与重氮酯的一锅串联反应，该反应通过分子间环丙烷化、开环和环化进行。