Issue 16, 2003
From the journal:

Chemical Communications

Stereoselective synthesis of 2,2-bis(C-branched-chain)glucopyranosid-3-ulose via an autoxidation–Michael addition reaction†

Hong-Min Liu,*a   Fuyi Zhanga  and  Da-Peng Zoua  

* Corresponding authors

a Department of Chemistry, Zhengzhou University, Zhengzhou, 450052, P. R. China
E-mail: liuhm@zzu.edu.cn.
Fax: +86-371-7767200
Tel: +86-371-7767200

Abstract

2,2-Bis(C-branched-chain)glucopyranosid-3-uloses, designed for the preparation of biologically active natural product iridoid derivatives, are synthesized selectively by the new reaction of butenolide-containing sugar with active methylene compounds, and the new reaction is clarified as autoxidation followed by Michael addition of carbanion.

Graphical abstract: Stereoselective synthesis of 2,2-bis(C-branched-chain)glucopyranosid-3-ulose via an autoxidation–Michael addition reaction

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Article information

DOI
https://doi.org/10.1039/B306227A
Article type
Communication
Submitted
03 Jun 2003
Accepted
27 Jun 2003
First published
04 Jul 2003

Chem. Commun., 2003, 2044-2045

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Stereoselective synthesis of 2,2-bis(C-branched-chain)glucopyranosid-3-ulose via an autoxidation–Michael addition reaction

H. Liu, F. Zhang and D. Zou, Chem. Commun., 2003, 2044 DOI: 10.1039/B306227A

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