一种构建羟基托烷骨架的新方法：(-)-包公藤 A 的对映选择性合成。

A new method for the construction of the hydroxylated tropane skeleton: enantioselective synthesis of (-)-Bao Gong Teng A.

机构信息

Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. China.

出版信息

Chem Commun (Camb). 2011 Feb 7;47(5):1545-7. doi: 10.1039/c0cc04371k. Epub 2010 Nov 25.

DOI:10.1039/c0cc04371k

PMID:21107467

Abstract

An efficient and highly diastereoselective method for the construction of the hydroxylated tropane skeleton is described. The method features a new intramolecular reductive coupling reaction of N-acyl N,O-acetal with aldehyde, cooperatively mediated by BF(3)·OEt(2) and SmI(2). On the basis of this method, a new enantioselective total synthesis of (-)-Bao Gong Teng A has been accomplished.

摘要

描述了一种高效且高度非对映选择性的构建羟基托烷骨架的方法。该方法的特点是新的 N-酰基 N,O-缩醛与醛的分子内还原偶联反应，由 BF(3)·OEt(2)和 SmI(2)共同介导。在此方法的基础上，完成了 (-)-宝公藤 A 的全新对映选择性全合成。