Norzoanthamine is a highly complex heptacyclic marine natural product isolated from colonial zoanthids of the genus Zoanthus sp. It potently inhibits the decrease of bone weight and strength in a postmenopausal osteoporosis mouse model, and represents a promising candidate for therapeutic development of anti-osteoporosis drugs. In order to enable mode of action studies and therapeutic development of this compound, we are developing a synthetic route that would allow efficient access to norzoanthamine and its simplified analogs. We completed an eleven-step enantioselective synthesis of its highly functionalized and stereochemically complex ABC carbocycle from ethyl acetoacetate. This synthetic route and other progresses toward the total synthesis of norzoanthamine will be presented.

Toward the total synthesis of norzoanthamine

242nd National Meeting (2011)

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