Ready access to the 6,8-dioxabicyclo[3.2.1]octane ring system using asymmetric heterocycloaddition induced by a chiral sulfoxide: application to the total synthesis of the Mus musculus pheromone |
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| Affiliation: | 1. Laboratoire de Physique et Chimie des Matériaux LPCM, Faculté des Sciences, Université Mouloud Mammeri, 15000 Tizi Ouzou, Algeria;2. Department of Chemistry, Faculty of Sciences, University Mohamed Bouguerra, Boumerdes, Algeria;3. Laboratoire de Physico-Chimie Théorique et de Chimie Informatique, Faculté de Chimie, USTHB, BP 32 El Alia, 16111 Bab-Ezzouar, Algiers, Algeria;4. Centre de Recherche Nucléaire de Draria (CRND), BP 43 Sebala, Draria, Algeria;5. Département du Génie de l''environnement, Ecole Nationale Polytechnique, 10 Avenue des Frères Ouadek, Hassen Badi, BP 182, 16200 El Harrach, Algiers, Algeria;6. QOPNA & LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal;7. Université de Reims Champagne Ardenne, CNRS, ICMR UMR 7312, 51097 Reims, France |
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| Abstract: | A new stereocontrolled total synthesis of the (1R,5S,7R)-exo-6,8-dioxabicyclo[3.2.1]oct-3-ene skeleton of the Mus musculus pheromone has been achieved via an asymmetric intermolecular Diels–Alder reaction and an intramolecular conjugated addition, controlled by a chiral auxiliary. |
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