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TOTAL SYNTHESIS OF HAMACANTHIN B CLASS MARINE BISINDOLE ALKALOIDS

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A method for the synthesis of 1-(1H-indol-3-yl)ethane-1,2-diamines, key synthetic precursors of a number of marine alkaloids, has been developed based on the reduction of adducts of O-benzylhydroxylamine and N-protected 3-(2-nitrovinyl)indoles.… Click to show full abstract

A method for the synthesis of 1-(1H-indol-3-yl)ethane-1,2-diamines, key synthetic precursors of a number of marine alkaloids, has been developed based on the reduction of adducts of O-benzylhydroxylamine and N-protected 3-(2-nitrovinyl)indoles. For the first time, the total synthesis of 6',6''-didebromohamacanthin B, 6'-debromohamacanthin B, and 6''-debromohamacanthin B, the secondary metabolites of the sponges Spongosorites and Discodermia calyx, was carried out.

Keywords: class marine; total synthesis; hamacanthin class; synthesis hamacanthin; marine bisindole; synthesis

Journal Title: Chemistry of Heterocyclic Compounds
Year Published: 2020

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