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Published on: November 9, 2019
DMD mediated formal synthesis of (+/-)-coerulescine
Oscar R Suárez-Castillo1, Myriam Meléndez-Rodríguez, Yaneth M A Contreras-Martínez
1Area Académica de Química, Universidad Autónoma del Estado de Hidalgo, Mineral de la Reforma, Hidalgo, 42184 México. osuarez@uaeh.edu.mx
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.
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