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

A new method for the construction of the hydroxylated tropane skeleton: enantioselective synthesis of (-)-Bao Gong Teng A
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构建羟基托烷骨架的新方法:对映选择性合成(-)-包公藤A

DOI:
10.1039/c0cc04371k
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发表时间:
2011-01-01
影响因子:
4.9
通讯作者:
Huang, Pei-Qiang
Huang, Pei-Qiang
中科院分区:
化学2区
文献类型:
--
作者:
Lin, Geng-Jie;Zheng, Xiao;Huang, Pei-Qiang

文献摘要

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描述了一种高效且高度非对映选择性的构造羟基化tropane骨架的方法。该方法采用BF(3)中心点OEt(2)和SmI(2)协同介导的N-酰基N, o -缩醛与醛的分子内还原偶联反应。在此基础上,完成了对映选择性全合成(-)-保宫藤a的新方法。
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)center dot OEt(2) and SmI(2). On the basis of this method, a new enantioselective total synthesis of (-)-Bao Gong Teng A has been accomplished.