title: Efficient synthesis of N-prenylpyrroloindoline and N-prenylindole alkaloids based on a new four-reaction anionic domino process.
abstract: 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.
authors.affiliation: Departamento de Química Organica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain.
authors.forename: Pilar
authors.initials: P
authors.lastname: López-Alvarado
authors.forename: Esmeralda
authors.initials: E
authors.lastname: Caballero
authors.forename: Carmen
authors.initials: C
authors.lastname: Avendaño
authors.forename: J Carlos
authors.initials: JC
authors.lastname: Menéndez
mesh_terms: D000838:Anions; D026121:Indole Alkaloids / Q000138:chemical synthesis*
chemical_list: D000838:Anions; D026121:Indole Alkaloids