A free radical route to syn lactones and other prostanoid intermediates in isoprostaglandin synthesis

Benoît Rondot; Thierry Durand; Jean Pierre Girard; Jean Claude Rossi; Laurent Schio; Subhash P. Khanapure; Joshua Rokach

doi:10.1016/S0040-4039(00)61401-6

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A free radical route to syn lactones and other prostanoid intermediates in isoprostaglandin synthesis

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A free radical route to syn lactones and other prostanoid intermediates in isoprostaglandin synthesis

Benoît Rondot, Thierry Durand, Jean Pierre Girard, Jean Claude Rossi, Laurent Schio, Subhash P. Khanapure et Joshua Rokach

Tetrahedron letters, Vol.34(51), pp.8245-8248

17/12/1993

DOI: https://doi.org/10.1016/S0040-4039(00)61401-6

Résumé

The hex-5-enyl radical cyclization methodology was applied to the formation of optical active prostanoid intermediates 7,8,9 with readily available diacetone-D-glucose as starting material. This result should lead to isoprostaglandins, a novel class of arachidonic acid metabolites obtained by a non-cyclooxygenase mechanism involving free radical-catalysed peroxidation of arachidonic acid. The Radical cyclization, applied to the thionocarbonate precursor from diacetone-D-glucose as starting material, give the optical active prostanoid intermediates.

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Titre: A free radical route to syn lactones and other prostanoid intermediates in isoprostaglandin synthesis
Créateurs - sans rôle: Benoît Rondot - Laboratoire de Chimie des Médiateurs et Physicochimie des Intéractions Biologiques associé au C.N.R.S., Université de Montpellier I, Faculté de Pharmacie 15 Av. Ch. Flahault, F-34060 Montpellier, France
Thierry Durand - Université de Montpellier
Jean Pierre Girard - Laboratoire de Chimie des Médiateurs et Physicochimie des Intéractions Biologiques associé au C.N.R.S., Université de Montpellier I, Faculté de Pharmacie 15 Av. Ch. Flahault, F-34060 Montpellier, France
Jean Claude Rossi - Laboratoire de Chimie des Médiateurs et Physicochimie des Intéractions Biologiques associé au C.N.R.S., Université de Montpellier I, Faculté de Pharmacie 15 Av. Ch. Flahault, F-34060 Montpellier, France
Laurent Schio - Claude Pepper Institute for Aging and Therapeutic Research, Florida Tech. (FIT), 150 W. University Blvd., Melbourne, FL 32901-6988, USA
Subhash P. Khanapure - Claude Pepper Institute for Aging and Therapeutic Research, Florida Tech. (FIT), 150 W. University Blvd., Melbourne, FL 32901-6988, USA
Joshua Rokach - Claude Pepper Institute for Aging and Therapeutic Research, Florida Tech. (FIT), 150 W. University Blvd., Melbourne, FL 32901-6988, USA
Détails de publication: Tetrahedron letters, Vol.34(51), pp.8245-8248
Éditeur: Elsevier Ltd
Nombre de pages: 4
Identifiants: 99138629009311
Unité académique: Institut des Biomolécules Max Mousseron - IBMM
Langue: English
Type de ressource: Journal article