Divergent approach to imino sugar C-glycosides using imino glycals: application to the stereocontrolled synthesis of (+)-deoxoprosophylline.
Tri-O-acetyl imino glucal 2 is readily made and shown to undergo a variety of Lewis acid mediated carbon-carbon bond forming reactions at C-1 of the piperidine nucleus. In all the reactions studied, the beta-anomer is predominant.
Dransfield
Paul J
PJ
School of Chemistry, University of Exeter, Exeter, Devon, UK EX4 4QD.
Gore
Paul M
PM
Shipman
Michael
M
Slawin
Alexandra M Z
AM