Application of acylpyridinium salt chemistry in the asymmetric synthesis of (-)-slaframine and 1-deoxynojirimycin and studies toward (+)-castanospermine

This research was directed towards the use of chiral N-acylpyridinium salt chemistry in the asymmetric synthesis of (−)-slaframine and (+)-castanospermine. The total synthesis of (−)-slaframine has been accomplished using a noval cycloselenocarbamation reaction. 1-Deoxynojirimycin was chosen as an interim goal for the synthesis of (+)-castanospermine. 1-Deoxynojirimycin contains 4 of the 5 stereocenters present in (+)-castanospermine. 1-Deoxynojirimycin's total synthesis was achieved. This along with other progress towards castanospermine is reported.