Total Synthesis of Hypersampsone M

Abstract

We report the first total synthesis of hypersampsone M, an archetypal member of the homoadamantane polycyclic polyprenylated acylphloroglucinols (PPAPs). Commencing from cyclohexenone, a key cyclopentene annulation followed by ring-expansion results in an elusive hydrazulene that undergoes a series of unexpected late-stage transformations, ultimately enabling completion of the synthesis. The route detailed herein represents a potentially general strategy for the synthesis of related homoadamantane PPAPs.

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