Hamman and co-workers recently isolated the alkaloid veranamine from the marine sponge V. rigida.[1] This compound has a unique 5,5-dimethyl dihydrobenzo[c][2,7]naphthyridine scaffold that shares key structural features with psychoactive beta-carbolines and cannabinoids. In a forced swim test, veranamine showed potent antidepressant activity. This presentation details our successful total synthesis of veranamine utilizing an unprecedented vinylogus Pictet-Gams cyclization. The gram-scale synthesis has enabled further biological evaluation. The route has also been employed to prepare several analogs for use in structure-activity relationship evaluation.<br/><br/>[1] Kochanaowska-Karamyan, A.J.; Hamann, M.T. Chem. Rev. 2010,110, 4489.

Gram scale total synthesis of veranamine

249th National Meeting (2015)

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