Producción Científica Profesorado

Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea



Suárez Castillo, Oscar Rodolfo

2001

Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea. Morales-Ríos M. S., Suárez-Castillo O. R., Trujillo-Serrato J. J., Joseph-Nathan P. DOI: 10.1021/jo0012647


Abstract


A general, efficient, and conceptually new approach to the total syntheses of marine-derived indole alkaloids, including ()-flustramines A (1) and B (2), ()-flustramides A (3) and B (4), and ()-debromoflustramine B (5), is outlined. The key step in the syntheses involves the conjugated addition of an organomagnesium species derived from prenyl bromide to 2-hydroxyindolenines. Compounds 1, 2, and 5 have been synthesized in five steps with 23%, 17%, and 16% overall yield, respectively, whereas flustramides 3 and 4 have been synthesized in only four steps with 24% and 18% overall yield, respectively, on the basis of 2-hydroxyindolenines.



Producto de Investigación




Artículos relacionados

Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters

Trapping enols of esters and lactones with diazomethane

One-potsynthesis of conformationallyrestrictedspirooxindoles

Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2

Synthesis of Indolylindolines Mediated by tert-BuNH2

Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives

Transesterifications mediated by t-BuNH2

Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea

Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles

Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural ...