Simple synthesis of phenylpropenoid β-D-glucopyranoside congeners based on Mizoroki-Heck type reaction of organoboron reagents

Palladium(II)-catalyzed carbon-carbon bond formation between allyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (3) and phenylboronic acid congeners gave the phenylpropenoid 2,3,4,6-tetra-O-acetyl-beta-D-glueopyranoside (4a-f) in good.yield. Among them, compounds 4a-c were converted to the naturally occurring phenylpropenoid beta-D-glucopyranoside analogues (1a-c). (c) 2005 Elsevier Ltd. All rights reserved.