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

Ruben L H AndringaNittert MarinusDaan V BuntElizabeth R HaidererRobert B AbramovitchChristopher D BrownKyu Y RheeMartin D WitteAdriaan J Minnaard
Published in: Chemical science (2024)
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.
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