Issue 63, 2013
From the journal:

Chemical Communications

Versatile construction of functionalized tropane ring systems based on lactamactivation: enantioselective synthesis of (+)-pervilleine B†

Su-Yu Huang,a   Zong Chang,a   Shi-Chuan Tuo,a   Long-Hui Gao,a   Ai-E Wanga  and  Pei-Qiang Huang*a  

* Corresponding authors

a Department of Chemistry, College of Chemistry and Chemical Engineering, and Fujian Provincial Key Laboratory of Chemical Biology, Xiamen University, Xiamen, Fujian 361005, China
E-mail: pqhuang@xmu.edu.cn
Tel: +86-592-2182240

Abstract

The halo-assisted intramolecular addition of silyl enol ethers with in situ activated lactams yielded (hydroxylated) 1-halo-8-azabicyclo[3,2,1]octane and 1-halo-9-azabicyclo[3,3,1]nonane ring systems, which provided an easy enantioselective access to 6β-silyloxytropane-3-one, 3α,6β-dihydroxytropane, and pervilleine B. The absolute configuration of the natural (−)-pervilleine B was determined to be 1R,3R,5S,6R.

Graphical abstract: Versatile construction of functionalized tropane ring systems based on lactam activation: enantioselective synthesis of (+)-pervilleine B

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Article information

DOI
https://doi.org/10.1039/C3CC43665A
Article type
Communication
Submitted
15 May 2013
Accepted
13 Jun 2013
First published
13 Jun 2013

Chem. Commun., 2013,49, 7088-7090

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Versatile construction of functionalized tropane ring systems based on lactam activation: enantioselective synthesis of (+)-pervilleine B

S. Huang, Z. Chang, S. Tuo, L. Gao, A. Wang and P. Huang, Chem. Commun., 2013, 49, 7088 DOI: 10.1039/C3CC43665A

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