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Total synthesis of arteannuin and deoxyarteannuin
Affiliation:1. The Division of Biology and Biomedical Sciences, Washington University in St Louis, United States;2. Dept. of Pharmaceutical Chemistry, College of Pharmacy, Prince Sattam Bin Abdulaziz University, Alkharj, Saudi Arabia;1. University of Dokuz Eylül, Department of Chemistry, Faculty of Science, 35160, Tınaztepe, Izmir, Turkey;2. Department of Pharmacy, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia;3. ENS Lyon, Université de Lyon, Laboratoire de Chimie de l’ENS Lyon, UMR 5182 CNRS-ENS Lyon, 46 allée d’Italie, 69364 Lyon, France;4. Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CO2-Glyco, UMR 5246, CNRS, Université Claude Bernard Lyon 1, Université de Lyon, 43 Boulevard du 11 Novembre 1918, F-6922 Villeurbanne, France;5. Gebze Technical University, Department of Chemistry, P.O. Box 141, 41400 Gebze, Kocaeli, Turkey;1. National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China;2. School of Chemistry, Chemical Engineering, and Biotechnology, Nanyang Technological University, Singapore 637371, Singapore;1. School of Pharmacy, Key Laboratory for Functional Substances of Chinese Medicine and Natural Medicine State, Anhui University of Chinese Medicine, Hefei, 230012, PR China;2. Anhui Medical College, Hefei, 230012, PR China;3. Anhui Province Key Laboratory of Research & Development of Chinese Medicine, Hefei, 230012, PR China;4. Institute of Medicinal Chemistry, Anhui Academy of Chinese Medicine, Hefei, 230012, PR China;5. State Key Laboratory for Quality Ensurance and Sustainable Use of Dao-di Herbs, Nation al Resource Center for Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing, 100700, PR China;6. Functional Activity and Resource Utilization on Edible and Medicinal Fungi Joint Laboratory of Anhui Province, Hefei, 230012, PR China;1. Nephrology Department, University Regional Hospital Center of Tours, 39, rue des Anguignis, bâtiment Le Coudray, résidence Le-Point-du-Jour, 45650 Saint-Jean Le Blanc, France;2. Internal Medicine Department, University Hospital Center of Libreville, BP 4009, Libreville, Gabon;3. Rheumatology Department, University Regional Hospital Center of Tours, 39, rue des Anguignis, bâtiment Le Coudray, résidence Le-Point-du-Jour, 45650 Saint-Jean Le Blanc, France;4. Infectiology Department, University Hospital Center of Libreville, BP 4009, Libreville, Gabon
Abstract:
Arteannuin 1 is a new sesquiterpene lactone containing a peroxide linkage and is an antimalarial principle isolated from Artemisia annua L. . R(+)-Citronellal 5 as a starting material for the total synthesis was converted into 11R(-)-methyl dihydroarteannuinate 12 in 14 steps. The key intermediate 4 was obtained from compound 12 in 5 steps. The introduction of hydroperoxide in 4 by photooxidation followed by acid treatment gave 1. Hydroxylation of 4 with osmium tetraoxide afforded deoxyarteannuin 2.
Keywords:
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