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.
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor
The absoluteconfiguration of cuauhtemone and related compounds
First Total Synthesis of ()-Flustraminol B
Regioselective Synthesis of 3-Indolyl(alkoxy)acetates
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Trapping enols of esters and lactones with diazomethane
Role of lipid peroxidation in biliary obstruction in the rat
Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea