Biomimetic Synthesis of Polycyclic Polyprenylated Acylphloroglucinol Natural Products Isolated from Hypericum papuanum

Biomimetic syntheses of three polycylic polyprenylated acylphloroglucinol natural products isolated from Hypericum papuanum, ialibinone A, ialibinone B, and hyperguinone B, have been accomplished by selective oxidative cyclizations of the proposed biosynthetic precursor 5, which was synthesized from phloroglucinol in three steps.