（+）-环麦角碱的不对称形式合成

Asymmetric formal synthesis of (+)-cycloclavine.

作者信息

Chen Jin-Quan, Song Le-Le, Li Feng-Xing, Shi Zi-Fa, Cao Xiao-Ping

机构信息

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, P. R. China.

出版信息

Chem Commun (Camb). 2017 Nov 30;53(96):12902-12905. doi: 10.1039/c7cc08044a.

DOI:10.1039/c7cc08044a

PMID:29110004

Abstract

The asymmetric synthesis of Szántay's amine (+)-2, the pivotal precursor for direct access to (+)-cycloclavine (1), is described for the first time in eleven steps with 19.7% overall yield from the commercially available 4-bromoindole. The strategy features an asymmetric induction by Ellman's sulfinimine and rhodium-catalysed isomerization of the C[double bond, length as m-dash]C bond.

摘要

首次报道了从市售的4-溴吲哚出发，经十一步反应以19.7%的总收率不对称合成Szántay胺（+）-2，它是直接制备（+）-环麦角碱（1）的关键前体。该策略的特色在于通过埃尔曼亚磺酰亚胺进行不对称诱导以及铑催化的C=C键异构化反应。