Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of naturalproducts
Meléndez Rodríguez, Myriam
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. DOI: 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 naturalproducts. This strategy allowed us to synthesize the naturalproduct1, 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 naturalproduct flustraminol B (7).
Artículos relacionados
Transesterifications mediated by t-BuNH2
Cleavage of alkoxycarbonylprotectinggroups from carbamates by t-BuNH2
First Total Synthesis of ()-Flustraminol B
Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives
Mechanisticstudies of the photochemicalrearrangement of 1-oxolongipin-2-ene derivatives
DFT and NMR parameterized conformation of valeranone
Photochemical rearrangements of highly functionalized longipinene derivatives