Isolation synthesis and glycosidase inhibition profile of 3-epi-casuarine |
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| Affiliation: | 1. Department of Organic Chemistry, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK;2. Institute of Grassland & Environmental Research, Plas Gogerddan, Aberystwyth SY23 3EB, Dyfed, Wales, UK;3. Glycobiology Institute, Department of Biochemistry, Oxford University, South Parks Road, Oxford OX1 3QU, UK;1. Instituto de Química Médica (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain;2. Department of Pharmacology, Medical School, University of Patras, 26500 Rio-Patras, Greece;1. Department of Pharmacy, Health and Nutrition Sciences, University of Calabria, 87036 Arcavacata di Rende, Cosenza, Italy;2. Université de Caen Basse-Normandie, Centre d’Etudes et de Recherche sur le Médicament de Normandie UPRES EA 4258 – FR CNRS 3038 INC3M, Bd Becquerel, 14032 Caen Cedex, France;3. Chemistry Department, Faculty of Science, Assiut University, 71516 Assiut, Egypt;4. Department of Pharmacy, University of Salerno, Via Giovanni Paolo II 132, 84084 Fisciano, Salerno, Italy;5. Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France;1. Laboratory for Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Ghent University, Harelbekestraat 72, B-9000 Gent, Belgium;2. Molecular Recognition Section, Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892, USA;1. Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, BS 10/1, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, Uttar Pradesh, India;2. Biochemistry Division, CSIR-Central Drug Research Institute, BS 10/1, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, Uttar Pradesh, India;3. Academy of Scientific and Innovative Research, New Delhi, India |
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| Abstract: | 3-epi-Casuarine, the first naturally occurring stereoisomer of casuarine, was isolated from Myrtus communis L. The glycosidase inhibition profile and NMR spectra of 3-epi-casuarine are compared with those of casuarine; the change in configuration at one of the six stereogenic centres causes a dramatic change in the conformation of the bicyclic system. The key step in the 6% overall yield synthesis of 3-epi-casuarine from d-gluconolactone is the efficient cyclization of a completely unprotected pentahydroxyaminomesylate to the pyrrolizidine nucleus. A low yield synthesis of casuarine is also reported. |
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