Issue 22, 2011
From the journal:

Organic & Biomolecular Chemistry

A concise stereoselective synthesis of (−)-erycibelline†

Zhao-Lan Zhang,ac   Shinpei Nakagawa,b   Atsushi Kato,b   Yue-Mei Jia,a   Xiang-Guo Hua  and  Chu-Yi Yu*a  

* Corresponding authors

a Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100191, China
E-mail: yucy@iccas.ac.cn

b Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan

c Graduate University of The Chinese Academy of Sciences, Beijing 100049, China

Abstract

(−)-Erycibelline, the dihydroxynortropane alkaloid isolated from Erycibe elliptilimba Merr. et Chun., was synthesized using a cyclic nitrone as advanced intermediate, wherein the key step was the SmI2-induced intramolecular reductive coupling of cyclic nitrone with aldehyde which resulted in good yield and stereoselectivity.

Graphical abstract: A concise stereoselective synthesis of (−)-erycibelline

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Article information

DOI
https://doi.org/10.1039/C1OB06244A
Article type
Paper
Submitted
25 Jul 2011
Accepted
11 Aug 2011
First published
12 Aug 2011

Org. Biomol. Chem., 2011,9, 7713-7719

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A concise stereoselective synthesis of (−)-erycibelline

Z. Zhang, S. Nakagawa, A. Kato, Y. Jia, X. Hu and C. Yu, Org. Biomol. Chem., 2011, 9, 7713 DOI: 10.1039/C1OB06244A

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