Issue 5, 2011
From the journal:

Chemical Communications

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

Geng-Jie Lin,a   Xiao Zhenga  and  Pei-Qiang Huang*ab  

* Corresponding authors

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

b The State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P.R. China
E-mail: pqhuang@xmu.edu.cn
Fax: +86 592 2186400
Tel: +86 592 2180992

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 BF3·OEt2 and SmI2. On the basis of this method, a new enantioselective total synthesis of (−)-Bao Gong Teng A has been accomplished.

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

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Article information

DOI
https://doi.org/10.1039/C0CC04371K
Article type
Communication
Submitted
12 Oct 2010
Accepted
08 Nov 2010
First published
25 Nov 2010

Chem. Commun., 2011,47, 1545-1547

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

G. Lin, X. Zheng and P. Huang, Chem. Commun., 2011, 47, 1545 DOI: 10.1039/C0CC04371K

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