Reactions of abietic acid methyl ester with m-chloroperbenzoic acid |
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| Affiliation: | 1. Chemistry Department, Federal University of Juiz de Fora, Cidade Universitária, São Pedro, Juiz de Fora, MG, 36036-900, Brazil;2. Laboratory of Synthesis of Natural Products and Drugs, Institute of Chemistry, University of Campinas - UNICAMP, P.O. Box 6154, 13083-970, Campinas, SP, Brazil;1. Laboratoire de Chimie et Physique Approche Multi-échelle de Milieux Complexes (LCP-A2MC), ICPM, Département de Chimie, Université de Lorraine, 1, Bd Arago, Metz-Technopôle, 57078 Metz, France;2. Université de Bourgogne Franche-Comté, Team ‘Biochemistry of the Peroxisome, Inflammation and Lipid Metabolism’ EA 7270/Inserm, Faculté des Sciences Gabriel, 6 Bd Gabriel, 21000 Dijon, France;3. Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran;1. Department of Chemistry, School of Physical Sciences, University of Nairobi, PO Box 30197, 00100 Nairobi, Kenya;2. Department of Chemistry, Egerton University, PO Box 536, 20115 Egerton, Kenya;3. National Centre for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, MS 38677, USA;4. Department of Biomolecular Sciences, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, MS 38677, USA;1. Key Laboratory of Plant Resources Conservation and Sustainable Utilization/Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, People’s Republic of China;2. Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou 510642, People’s Republic of China;1. Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, 46100 Burjassot, València, Spain |
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| Abstract: | Abietic acid methyl ester reacts regioselectively with m-chloro-perbenzoic acid, in the presence of water to yield a mixture of the two epimeric 13,14-monoepoxides. These epoxides further react affording a mixture of 1,2- and 1, 4-unsaturated diols, The overall yield of the reaction is acceptably good (70–80%). The formation of these and other products are discussed. |
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