Total synthesis of (+)-(S)-angustureine and the determination of the absolute configuration of the natural product angustureine |
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| Affiliation: | 1. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severny Proezd, 142432 Chernogolovka, Moscow Region, Russian Federation;2. Centre for Theoretical and Computational Chemistry (CTCC), Department of Chemistry, University of Oslo, P.O. Box 1033 Blindern, N-0315 Oslo, Norway;3. Department of Chemistry, M.V. Lomonosov Moscow State University, 1 Leninskie Gory, 119991 Moscow, Russian Federation;1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China;2. Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018 San Sebastián, Spain;3. Japan Synchrotron Radiation Research Institute, SPring-8, 1-1-1 Kouto, Sayo-gun, 679-5198 Sayo-cho, Hyogo, Japan;4. Department of Chemistry and Materials Science, Tokyo Institute of Technology, Ookayama 2, Meguro-ku, Tokyo 152-8551, Japan;5. National Institute of Advanced Industrial Science and Technology (AIST), Anagahora 2266-98, Shimoshidami, Moriyama, 463-8560 Nagoya, Aichi, Japan;6. IKERBASQUE, Basque Foundation for Science, María Díaz de Haro 3, 48013 Bilbao, Spain;7. Department of Chemistry, University of Turku, Vatselankatu 2, FIN-20014 Turku, Finland;8. Molecular Structure Analysis, German Cancer Research Center (DKFZ), Im Neuenheimer Feld 280, D-69009 Heidelberg, Germany;1. Department of Chemistry, Payame Noor University, Tehran, Iran;2. Department of Chemistry, Gobardanga Hindu College, 24-Parganas (North), India |
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| Abstract: | 
Angustureine, isolated from the bark of Galipea officinalis Hancock, is a novel quinoline alkaloid with a n-pentyl side chain at the 2-position. The total synthesis of (+)-(S)-angustureine and a determination of the absolute configuration of the natural product angustureine were achieved using ring-closing metathesis (RCM) and the Mitsunobu reaction as key steps. |
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