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
Role of lipid peroxidation in biliary obstruction in the rat
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine
Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea
Synthesis of Bromoindole Alkaloids from Laurencia brongniartii
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Synthesis of Indolylindolines Mediated by tert-BuNH2
First Total Synthesis of ()-Flustraminol B
Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives