Chemoenzymatic syntheses of (−)-1-deoxymannojirimycin (DMJ) and its naturally occurring 6-O-α-l-rhamnopyranosyl glycoside
Martin G. Banwell,Xinghua Ma,Naoki Asano,Kyoko Ikeda,John N. Lambert
Organic & Biomolecular Chemistry Pub Date : 05/19/2003 00:00:00 , DOI:10.1039/B304063A
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