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

13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

Trapping enols of esters and lactones with diazomethane

Synthesis of Indolylindolines Mediated by tert-BuNH2

Transesterifications mediated by t-BuNH2

Role of lipid peroxidation in biliary obstruction in the rat

Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine

Reactivity of TpMe2Ir(C2H4)(DMAD) with carboxylic acids. A DFT study on geometrical isomers and stru...

Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2

One-potsynthesis of conformationallyrestrictedspirooxindoles