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.
The absoluteconfiguration of cuauhtemone and related compounds
Role of lipid peroxidation in biliary obstruction in the rat
Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor
Synthesis of Bromoindole Alkaloids from Laurencia brongniartii
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters
Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase
Transesterifications mediated by t-BuNH2
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