Producción Científica Profesorado

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).



Producto de Investigación




Artículos relacionados

One-potsynthesis of conformationallyrestrictedspirooxindoles

Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2

Regioselective Synthesis of 3-Indolyl(alkoxy)acetates

Synthesis of Bromoindole Alkaloids from Laurencia brongniartii

Trapping enols of esters and lactones with diazomethane

Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives

Transesterifications mediated by t-BuNH2

Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea

Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling

Synthesis of Indolylindolines Mediated by tert-BuNH2