ol400735z_si_002.pdf (469.63 kB)

Asymmetric Syntheses of (−)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin via a Ring-Expansion Approach

Download (469.63 kB)
journal contribution
posted on 19.02.2016 by Stephen G. Davies, Aude L. A. Figuccia, Ai M. Fletcher, Paul M. Roberts, James E. Thomson
The asymmetric syntheses of (−)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin are described herein. The ring-closing iodoamination of two epimeric bishomoallylic amines to give the corresponding 5-iodomethylpyrrolidines was followed by in situ ring-expansion to give two diastereoisomerically pure (>99:1 dr) cyclic carbonates. Subsequent deprotection gave (−)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin as single diastereoisomers in 7.4 and 3.3% overall yield, respectively, from commercially available starting materials.

History

Exports