Issue 31, 2009
From the journal:

Chemical Communications

From vinylpyranoses to carbasugars by an iron-catalyzed reaction complementary to classical Ferrier carbocyclization†

Dinh Hung Mac,a   Ramesh Samineni,ab   Julien Petrignet,a   Pabbaraja Srihari,b   Srivari Chandrasekhar,b   Jhillu Singh Yadav*b  and  René Grée*a  

* Corresponding authors

a Université de Rennes 1, Laboratoire de Chimie et Photonique Moléculaires, CNRS UMR 6510, Avenue du Général Leclerc, 35042 Rennes Cedex, France
E-mail: rene.gree@univ-rennes1.fr
Fax: (33) (0) 2 23 23 69 78
Tel: (33) (0) 2 23 23 57 15

b Indian Institute of Chemical Technology, Hyderabad, India
E-mail: yadavpub@iict.res.in
Fax: 914027150387
Tel: 914027193030

Abstract

Starting from vinylpyranoses an iron-catalyzed tandem isomerization–intramolecular aldolization reaction was developed to prepare cyclohexenone derivatives bearing substituents on the double bond, and it has been applied in a short synthesis of 4-epi-gabosines A and B, from D-glucose.

Graphical abstract: From vinylpyranoses to carbasugars by an iron-catalyzed reaction complementary to classical Ferrier carbocyclization

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Article information

DOI
https://doi.org/10.1039/B907632H
Article type
Communication
Submitted
15 Apr 2009
Accepted
10 Jun 2009
First published
24 Jun 2009

Chem. Commun., 2009, 4717-4719

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From vinylpyranoses to carbasugars by an iron-catalyzed reaction complementary to classical Ferrier carbocyclization

D. H. Mac, R. Samineni, J. Petrignet, P. Srihari, S. Chandrasekhar, J. S. Yadav and R. Grée, Chem. Commun., 2009, 4717 DOI: 10.1039/B907632H

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