%0 Journal Article
%A López-Alvarado Gutiérrez, María Pilar
%A Caballero, Esmeralda
%A Avendaño López, María Carmen
%A Menéndez Ramos, José Carlos
%T Efficient Synthesis of N-Prenylpyrroloindoline and N-Prenylindole Alkaloids Based on a New Four-Reaction Anionic Domino Process
%D 2006
%U https://hdl.handle.net/20.500.14352/133338
%X Treatment of 2,5-diketopiperazines or carbamates derived from tryptophan or tryptamine with iodomethyltrimethylsilane followed by lithium hexamethyldisilazane and a prenyl halide produced stereoselectively derivatives of the hexahydropyrrolo[2,3-b]indole system bearing prenyl substituents both at C-3a and at the indoline nitrogen in a one-pot procedure involving a novel four-reaction anionic domino process. The reaction was applied to the preparation of N-prenyltryprostatin B and to achieving a very efficient formal total synthesis of the biologically active marine natural product (±)-debromoflustramine B.
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