DMD mediated formal synthesis of (+/-)-coerulescine.
A highly efficient method for the formal synthesis of the natural product (+/-)-coerulescine 1 from tetrahydro-beta-carboline 3, mediated by dimethyldioxirane (DMD), is described. Compound 15, the N9-demethylated precursor of 1, was prepared from 3 in 4 steps with an overall yield of 95%. The effect of electron withdrawing groups at the N2,N9 atoms of 3 was explored for the oxidative rearrangement step.
Suárez-Castillo
Oscar R
OR
Area Académica de Química, Universidad Autónoma del Estado de Hidalgo, Mineral de la Reforma, Hidalgo, 42184 México. osuarez@uaeh.edu.mx
Meléndez-Rodríguez
Myriam
M
Contreras-Martínez
Yaneth M A
YM
Alvarez-Hernández
Alejandro
A
Morales-Ríos
Martha S
MS
Joseph-Nathan
Pedro
P
D000814:Aniline Compounds / Q000138:chemical synthesis*; D002243:Carbolines / Q000737:chemistry*; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure
D000814:Aniline Compounds; D002243:Carbolines; D004852:Epoxy Compounds; C480174:coerulescine; C009804:tryptoline; C064455:dimethyldioxirane