Thapsigargin is a complex densely oxygenated sesquiterpene lactone, which functions as a selective and irreversible subnanomolar inhibitor of sarco/endoplasmic reticulum Ca2+ ATPases (SERCAs). Moreover, a prodrug of the natural product is currently in phase II clinical trials for the treatment of several forms of cancer. Nevertheless, the natural product is isolated in low yield from the Mediterranean plant Thapsia garganica L. that is not easily cultivated. This seminar will report the development of a scalable 14-step synthesis of thapsigargin from commercially available (R)-(–)-carvone. We envision that this route will also permit the construction of related members of the family and structural analogs.

14-Step total synthesis of thapsigargin from (R)-(–)-carvone

253rd National Meeting (2017)

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