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Synlett 1997; 1997(SI): 533-534
DOI: 10.1055/s-1997-6112
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Asymmetric Synthesis of L-Deoxymannojirimycin

A. I. Meyers* , David A. Price, C. J. Andres
  • *Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523-1872, U.S.A., Fax 970 491 2114; aimeyers@lamar.colostate.edu
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Publication History

Publication Date:
31 December 2000 (online)

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Starting from dihydropyran 1, the chiral lactam 4 was rapidly obtained. Following unsaturation, highly diastereoselective allylic oxidation and dihydroxylation furnished lactam 7 from which the azasugar, L-deoxymannojirimycin, could be prepared.

allylic oxidation - dihydroxylation - chiral lactam - chiral piperidines - phenyl glycinol