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■ Stereoselective Synthesis of D-1-Deoxynojirimycin and Its Stereoisomers

In Su Kim, Ho Young Lee, and Young Hoon Jung*

*College of Pharmacy, Sung Kyun Kwan University, 300 Jangangu, Chonchondong, Suwon 440-746, Korea

Abstract

A stereoselective synthesis of D-1-deoxynojirimycin (1), D-1-deoxymannojirimycin (2), and D-1-deoxyallonojirimycin (3) was achieved via the regioselective and diastereoselective amination of anti-1,2-dibenzyl ether using chlorosulfonyl isocyanate (CSI), ring-closing metathesis, diastereoselective dihydroxylation, and the regioselective stereochemical inversion of the resulting diol.