Issue 12, 2003
From the journal:

Organic & Biomolecular Chemistry

Chemoenzymatic syntheses of (−)-1-deoxymannojirimycin (DMJ) and its naturally occurring 6-O-α-l-rhamnopyranosyl glycoside

Martin G. Banwell,*a   Xinghua Ma,a   Naoki Asano,b   Kyoko Ikedab  and  John N. Lambertc  

* Corresponding authors

a Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia
E-mail: mgb@rsc.anu.edu.au

b Department of Biochemistry, Faculty of Pharmaceutical Sciences, Hokuriku University, Kanagawa-machi, Kanazawa 920-1181, Japan

c Biota Chemistry Laboratory, Chemistry Department, Monash University, Clayton, Victoria 3168, Australia

Abstract

The naturally occurring sugar mimetic alkaloids 1-deoxymannojirimycin (DMJ, 1) and 6-O-α-L-rhamnopyranosyl-DMJ (2) have each been prepared in a completely stereoselective manner from the cis-1,2-dihydrocatechol 3, itself obtained in enantiomerically pure form by microbial oxidation of chlorobenzene.

Graphical abstract: Chemoenzymatic syntheses of (−)-1-deoxymannojirimycin (DMJ) and its naturally occurring 6-O-α-l-rhamnopyranosyl glycoside

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Article information

DOI
https://doi.org/10.1039/B304063A
Article type
Communication
Submitted
16 Apr 2003
Accepted
13 May 2003
First published
19 May 2003

Org. Biomol. Chem., 2003,1, 2035-2037

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Chemoenzymatic syntheses of (−)-1-deoxymannojirimycin (DMJ) and its naturally occurring 6-O-α-L-rhamnopyranosyl glycoside

M. G. Banwell, X. Ma, N. Asano, K. Ikeda and J. N. Lambert, Org. Biomol. Chem., 2003, 1, 2035 DOI: 10.1039/B304063A

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