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