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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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