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
Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles
Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling
Trapping enols of esters and lactones with diazomethane
Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea
The absoluteconfiguration of cuauhtemone and related compounds
One-potsynthesis of conformationallyrestrictedspirooxindoles
13C NMR and crystallographic evidence of push-pull effects in furoindolic ?-enamino esters