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.
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Synthesis of Bromoindole Alkaloids from Laurencia brongniartii
First Total Synthesis of ()-Flustraminol B
Role of lipid peroxidation in biliary obstruction in the rat
Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea
Trapping enols of esters and lactones with diazomethane
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles