Producción Científica Profesorado

DMD mediated formal synthesis of (+/-)-coerulescine



Alvarez Hernandez, Alejandro

2009

Suárez-Castillo Oscar R., Meléndez-Rodríguez Myriam, Contreras-Martínez Yaneth M. A., Álvarez-Hernández Alejandro, Morales-Ríos Martha S., Joseph-Nathan Pedro.DMD Mediated Formal Synthesis of ()-Coerulescine. Nat. Prod. Commun. 4, 797802 (2009). ISSN 1934-578X.


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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