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.






Artículos relacionados

Addition reaction of benzylbenzylidenenamine to lithium enolates of 1,3-dioxolan-4-one: synthesis of...

Furocoumarins of three species of the genus Dorstenia

Diastereoselective alkylation of chiral glycinate derivatives containing the ?-phenylethyl group.

Bis(acetylsalicylato-j2O,O00)diaquacadmium(II)

Synthesis of New Chiral Derivatives of N,N?-Dimethylpropyleneurea (DMPU) and Examination of Their In...

Stereoselective addition of allylmagnesium chloride to the CN bond of [4.3.0] boron heterobicycles

Diastereoselective Synthesis of Spiro-?-lactams via Staudinger Reaction

Comparative Structural Characterization of the Biquaternized N-CH3 and N-BH3 Derivatives of the cis-...

Preparation of N-aryl-substituted spiro-?-lactams via Staudinger cycloaddition

An efficient potassium cyanide-promoted synthesis of 2-arylbenzoxazoles from [4.3.0]boron heterobicy...