Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural products
Suárez Castillo, Oscar Rodolfo
2006
Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural products. Oscar R. Suárez-Castillo, Maricruz Sánchez-Zavala, Myriam Meléndez-Rodríguez, Luis E. Castelán-Duarte, Martha S. Morales-Ríos, Pedro Joseph-Natha. http://dx.doi.org/10.1016/j.tet.2006.01.036
Abstract
This work describes a general protocol for the oxidation of indole and oxindole derivatives with dimethyldioxirane to give 3-hydroxyoxindoles present in many natural products. This strategy allowed us to synthesize the natural product 1, to carry out the first total synthesis of 4, a formal total synthesis of donaxaridine (5) and to achieve the synthesis of pyrroloindoline 8, a debromo analogue of the natural product flustraminol B (7).
Artículos relacionados
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea
First Total Synthesis of ()-Flustraminol B
Regioselective Synthesis of 3-Indolyl(alkoxy)acetates
Role of lipid peroxidation in biliary obstruction in the rat