Hyperhexanone A, a crucial intermediate from bicyclo[3.3.1]- to cyclohexanone monocyclic-polycyclic polyprenylated acylphloroglucinols

Hyperhexanones A (1) and B (2), two novel polycyclic polyprenylated acylphloroglucinol (PPAPs) derivatives, were isolated from Hypericum sampsonii. Compound 1 possesses a novel 1,2-seco-bicyclo[3.3.1]-PPAP skeleton, which represents a crucial intermediate from bicyclo[3.3.1]-PPAPs to the peculiar cyclohexanone monocyclic-PPAPs (CM-PPAPs). A plausible biogenetic pathway was proposed to discuss the origins of the CM-PPAPs.

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