Total synthesis of dissectol A, using an enediolate-based Tsuji-Trost reaction

Dissectol A is a rearranged terpene glycoside isolated from several flowering plants. Starting from glucose, the densely functionalized bicyclic structure has been prepared via site-selective oxidation and an intramolecular allylic alkylation reaction with an enediolate as the nucleophile. Despite earlier reports, dissectol A is not effective at inhibiting DevRS signaling in whole-cell Mycobacterium tuberculosis and does not inhibit growth of the bacterium. The densely functionalized terpene glycoside dissectol A has been prepared via site-selective oxidation and an intramolecular Tsuji-Trost allylic alkylation reaction with an enediolate as the nucleophile.