Total Synthesis of Calanthoside, a Potential Hair Growth Stimulant: A Facile Synthetic Approach via One-Pot S- and O-Glucosidic Bond Formation

The article presents the first total synthesis of calanthoside, a compound with significant proliferative activity on human hair follicle dermal papilla cells, achieved through a seven-step process with a 43% overall yield. The synthesis involves a one-pot method for forming S- and O-glucosidic bonds, utilizing a nucleophilic substitution reaction and enol-glucosylation to construct the S-,O-bisdesmoside structure. This approach demonstrates broad substrate adaptability, achieving approximately 84% yield for S,O-bisglycoside intermediates with various sugar donors beyond d-glucose.