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

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

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

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

The absoluteconfiguration of cuauhtemone and related compounds

First Total Synthesis of ()-Flustraminol B

One-potsynthesis of conformationallyrestrictedspirooxindoles

Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine

Cascade [1,3]-Sigmatropic Rearrangements of Ketene O,O-Acetals: Kinetic and DFT Level Mechanistic St...

Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor

Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling