Enantioselective Synthesis of Manzamine A

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DESCRIPTION (provided by applicant): This project entails the development of a double mannich cascade approach to the synthesis of the manzamine alkaloids. The manzamines have a unique structure, not found in other natural products, and they possess noteworthy biological activity. Manzamine A, in particular, possesses significant antitumor and antimalarial activity. Its natural source is limited, so in order for the biological activity of manzamine A to be further explored, an efficient method for its total synthesis must be developed. Manzamine A has succumbed to only 2 total syntheses since its isolation in 1986 from a marine sponge. The scaffold of this challenging molecule is approachable via the proposed transannular double mannich cascade. This strategy will be applied toward the enantioselective total synthesis of manzamine A, and would be applicable to others in the manzamine family. The efficient and convergent strategy proposed would provide a novel access point to this valuable family of natural products.