A Short and Efficient Synthesis of 2R,3R,4R-3,4-Dihydroxyproline, 1,4-Dideoxy-1,4-imino-l-xylitol, 2R,3R,4R,5S-3,4,5-Trihydroxypipecolic Acid, and 1,5-Dideoxy-1,5-imino-l-iditol

Abstract

The syntheses of pyrrolidine alkaloids (-)-1 and (+)-3 were accomplished in 47% and 60% overall yield from 2-azido-2-deoxy-l-idonate 5, while piperidine alkaloids (-)-2 and (+)-4 were obtained in 51% and 53% overall yield from the same starting material. Key step includes iodine promoted one-pot cyclization, and selective deprotection of isopropylidene and 9-phenylfluoren-9-yl (Pf) group.