Indole alkaloids are of prominence because of their resemblance with various biologically essential molecules including tryptophan, tryptamine, and serotonin. The Sarpagin type indole alkaloids comprise one of the most diverse series of indole alkaloid natural products. These indole alkaloids are primarily isolated from three plant families: Apocynaceae, Rubiaceae, and Loganiaceae which have been used in traditional and folk medicines in many countries around the world. Biological screening of these alkaloids is not always possible, presumably, due to the paucity of the isolated natural products. However, some of the alkaloids from this group of structurally related alkaloids have been shown to possess important biological activity. Considering the useful bioactivity and complex structural features, the total synthesis of these alkaloids is of great importance. Some key transformations in our strategy include the diastereospecific asymmetric Pictet-Spengler cyclization, diastereospecific Dieckmann condensation, and an enolatedriven palladium catalyzed cross-coupling process. The progress toward the total synthesis of hystrixnine, gelsempervines A and B will be presented.

Progress toward the enantiospecific and stereospecific total synthesis of a number of sarpagine-related indole alkaloids including hystrixnine and gelsempervines A and B

256th National Meeting (2018)

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