Simple syntheses of L-fucopyranose and fucosidase inhibitors utilizing the highly stereoselective methylation of an arabinofuranoside 5-urose derivative

Abstract

The simple syntheses of L-fucopyranose 1 and its three analogues 2–4 are described. A key reaction is a stereocontrolled elongation by one carbon unit at the side chain of an α-D-arabino-pentodialdo-1,4-furanoside 9 with MeMgI–ZnCl₂ or Me₃Al. Diastereofacial selectivities of more than 92% were achieved.