Synthesis of indole alkaloid analogues: novel domino stereoselective electrophile addition--cyclizations of tryptophan-derived alpha-amino nitriles.
The synthesis of new indole alkaloid analogues, containing a 1,2,4,5,10b,10c-hexahydropyrrolo[1',2',3':1,9a,9]imidazo[1,2-a]indole skeleton, via highly stereoselective novel domino cyclative halogenation or prenylation reactions of tryptophan-derived alpha-amino nitriles, is described.
González-Vera
Juan A
JA
Instituto de Química Médica (CSIC), Juan de la Cierva 3, E-28006 Madrid, Spain.
García-López
M Teresa
MT
Herranz
Rosario
R
D000586:Amination; D001966:Bromine / Q000737:chemistry; D002713:Chlorine / Q000737:chemistry; D003500:Cyclization; D004583:Electrons; D007093:Imidazoles / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*
D007093:Imidazoles; D026121:Indole Alkaloids; D009570:Nitriles; D002713:Chlorine; D014364:Tryptophan; D001966:Bromine