Artículos de revistas
An approach for the enantioselective synthesis of biologically active furanones from a Morita-Baylis-Hillman adduct
Registro en:
Tetrahedron. Pergamon-elsevier Science Ltd, v. 66, n. 34, n. 6749, n. 6753, 2010.
0040-4020
WOS:000280953500007
10.1016/j.tet.2010.06.077
Autor
Amarante, GW
Coelho, F
Institución
Resumen
Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Herein, we disclose an approach for the asymmetric synthesis of both enantiomers of an anti-inflammatory furanone. The approach is based on the utilization of a Morita-Baylis-Hillman adduct as starting material and has as key step a selective epoxide-opening/benzylic oxidation mediated by Palladium (II). This sequence afforded an advanced intermediate, which was used to accomplish the total synthesis. Experimental evidences allowed us to suggest a mechanistic proposal for the oxidation Palladium(II)-mediated. (C) 2010 Elsevier Ltd. All rights reserved. 66 34 6749 6753 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)