Selenium-Iodine Cooperative Catalyst for Chlorocyclization of Tryptamine Derivatives.

Chlorocyclization of tryptamine derivatives has been developed with the use of a diphenyl diselenide-iodine cooperative catalyst. Various tryptamine derivatives can be smoothly converted to the corresponding C3a-chlorohexahydropyrrolo[2,3-b]indoles. Additionally, we demonstrate the formal total syntheses of (-)-psychotriasine and (-)-acetylardeemin by introducing nucleophiles to the C3a position of the products.