Stereochemistry of terpene derivatives. Part 4: Fragrant terpenoid derivatives with an unsaturated gem-dimethylbicyclo[3.1.0]hexane system |
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| Institution: | 1. Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland;2. Department of Chemistry, Agricultural University, Norwida 25, 50-375 Wrocław, Poland;3. Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50-383 Wrocław, Poland;1. Advanced Biomedical Computing Center, SAIC-Frederick, Inc., Information Systems Program, Frederick National Laboratory for Cancer Research (FNLCR), Frederick, MD 21702, USA;2. Laboratory of Clinical Investigation, Intramural Research Program, National Institute on Aging, NIH, 251 Bayview Boulevard, Baltimore, MD 21224, USA;3. School of Chemistry, University of Leeds, Leeds LS2 9JT, UK;4. School of Biomedical Sciences, University of Leeds, Leeds LS2 9JT, UK;5. Department of Biomedical Sciences, Chang Gung University, 259 Wen-Hwa 1st Road, Kwei-Shan, Taiwan;1. Department of Chemistry, Fudan University, Shanghai 200433, PR China;2. School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai 201203, PR China;3. Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Chinese Academy of Sciences, PR China;1. Latvian Institute of Organic Synthesis, 21 Aizkraukles, LV-1006 Riga, Latvia;2. Faculty of Chemistry, University of Latvia, 48 Kr. Valdemara, LV-1013 Riga, Latvia;1. Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India;2. JNCASR, Jakkur, Bangalore 560064, India |
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| Abstract: | Starting from (+)-3-carene 1 several chiral fragrant compounds with the bicyclo3.1.0]hexane system 4–6 and 10–20 were synthesized. These compounds are structural analogues of naturally occurring fragrant compounds, such as ionones and damascones, and possess either an endo- or an exo-cyclic double bond in the bicyclo3.1.0]hexane moiety. The absolute configuration of selected products was confirmed by X-ray crystallography and circular dichroism analysis. |
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