Add time:08/28/2019         Source:sciencedirect.com

Herein, we describe an expedient synthesis of the hexaoxygenated guaianolide thapsigargin (1), a potent inhibitor of the sarco/endoplasmic reticulum Ca2+-ATPase (SERCA), from the natural product nortrilobolide (2). This protocol involves three key steps: the one-pot substitution-oxidation reaction of an allylic ester into its corresponding α,β-unsaturated ketone, subsequent stereoselective α′-acyloxylation in the presence of Mn(OAc)3, and a highly stereoselective ketone reduction.

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