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.
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor
Role of lipid peroxidation in biliary obstruction in the rat
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Regioselective Synthesis of 3-Indolyl(alkoxy)acetates
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters