title: DMD mediated formal synthesis of (+/-)-coerulescine.
abstract: 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.
authors.affiliation: Area Académica de Química, Universidad Autónoma del Estado de Hidalgo, Mineral de la Reforma, Hidalgo, 42184 México. osuarez@uaeh.edu.mx
authors.forename: Oscar R
authors.initials: OR
authors.lastname: Suárez-Castillo
authors.forename: Myriam
authors.initials: M
authors.lastname: Meléndez-Rodríguez
authors.forename: Yaneth M A
authors.initials: YM
authors.lastname: Contreras-Martínez
authors.forename: Alejandro
authors.initials: A
authors.lastname: Alvarez-Hernández
authors.forename: Martha S
authors.initials: MS
authors.lastname: Morales-Ríos
authors.forename: Pedro
authors.initials: P
authors.lastname: Joseph-Nathan
mesh_terms: D000814:Aniline Compounds / Q000138:chemical synthesis*; D002243:Carbolines / Q000737:chemistry*; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000814:Aniline Compounds; D002243:Carbolines; D004852:Epoxy Compounds; C480174:coerulescine; C009804:tryptoline; C064455:dimethyldioxirane