Boronic Acid-Catalyzed Final-Stage Site-Selective Acylation for the Total Syntheses of O-3′-Acyl Bisabolol β-D-Fucopyranoside Natural Products and Their Analogues

Abstract

The first concise total syntheses of O-3′-senecioyl α-bisabolol β-D-fucopyranoside (4a) and O-3′-isovaleroyl α-bisabolol β-D-fucopyranoside (4b) were achieved through final-stage site-selective acylation via the activation of cis-vicinal diols by imidazole-containing boronic acid catalysts as a key step. This synthetic method was also effective for the syntheses of unnatural analogues with modified acyl side chains or carbohydrate moiety.

Graphical Abstract