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.
Regioselective Synthesis of 3-Indolyl(alkoxy)acetates
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Transesterifications mediated by t-BuNH2
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
First Total Synthesis of ()-Flustraminol B
Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2