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

The first total synthesis of calanthoside ( 1 ), which exhibits potent proliferative activity against human hair follicle dermal papilla cells, has been achieved in seven steps with an overall yield of 43% on a gram scale starting from anthranilic acid ( 11 ). The synthetic strategy features a one-pot process involving thioglucoside bond formation via nucleophilic substitution reaction and enol-glucosylation for building the S -, O -bisdesmoside structure of 1 . Moreover, the one-pot reaction showed broad substrate adaptability to several sugar donors other than d-glucose, thus affording S , O -bisglycoside intermediates in ∼84% yield.