2006
Synthesis of Bromoindole Alkaloids from Laurencia brongniartii. Oscar R. Suárez-Castillo, Lidia Beiza-Granados, Myriam Meléndez-Rodríguez, Alejandro Álvarez-Hernández, Martha S. Morales-Ríos, Pedro Joseph-Nathan. DOI: 10.1021/np060406a
Abstract
A regioselective synthesis of N-carbomethoxy-2,3,5-tribromoindole (6) via a sequential one-pot bromination?aromatization?bromination of N-carbomethoxyindoline (2) is described. The process for the transformation of 2 into 6 permitted the isolation of stable reaction intermediates N-carbomethoxy-5-bromoindoline (3), N-carbomethoxy-5-bromoindole (4), and N-carbomethoxy-3,5-dibromoindole (5). Compound 6 was used to complete the total synthesis of the natural products 1b and 1c. In addition, bromination of N-carbomethoxyindole (11) afforded N-carbomethoxy-2,3,6-tribromoindole (13), from which the natural product 1a was synthesized.
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Role of lipid peroxidation in biliary obstruction in the rat
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
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