Concise and highly stereoselective syntheses of d-fagomine and 2-epi-fagomine.

Highly stereoselective total syntheses of polyhydroxylated piperidines d -fagomine and 2- epi -fagomine have been developed starting from 3,4,6-tri- O -benzyl- d -glucal which is a derivative of d -Glucose. Key steps in the synthesis of these azasugars involved N -Boc-protected amine preparation from oxime followed by stereo specific iodination of alcohol and cascade cyclization triggered by N -Boc deprotection. [ABSTRACT FROM AUTHOR]