Synthesis of (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol,the aggregation pheromone of the ambrosia beetle Platypus quercivorus,its racemate, (1R,4R)- and (1S,4S)-isomers |
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| Affiliation: | 1. School of Chemistry, University of Wales, Bangor, Gwynedd, LL57 2UW, UK;2. PhytoQuest Limited, Plas Gogerddan, Aberystwyth, Ceredigion, SY23 3EB, UK;3. UK National Crystallography Service, Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ, UK;1. School of Pharmacy, National Cheng Kung University Hospital, College of Medicine, National Cheng Kung University, Tainan 701, Taiwan, ROC;2. Department of Biotechnology, National Formosa University, Yunlin 632, Taiwan, ROC;3. Department of Medical Technology, Chung Hua University of Medical Technology, Tainan 717, Taiwan, ROC;4. Graduate Institute of Natural Products, Chang Gung University, Taoyuan 333, Taiwan, ROC;5. Chinese Herbal Medicine Research Team, Healthy Aging Research Center, Chang Gung University, Taoyuan 333, Taiwan, ROC;6. Department of Pharmacy, Tajen University, Pintung 907, Taiwan, ROC;7. Department of Surgery, and Institute of Biomedical Engineering, National Cheng Kung University, Medical Center and Medical School, Tainan 701, Taiwan, ROC;8. Department of Anesthesiology, and Institute of Biomedical Engineering, National Cheng Kung University, Medical Center and Medical School, Tainan 701, Taiwan, ROC;9. Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, USA;10. Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung 401, Taiwan, ROC |
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| Abstract: | (S)-Perillyl alcohol was converted to (R)-cryptone (91.5–93% ee) in six steps, which was then treated with methyllithium to give (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus. The racemic pheromone was also prepared by methylation of (±)-cryptone. Both (1R,4R)- and (1S,4S)-isomers (98% ee) of the pheromone were synthesized from the enantiomers of dihydrolimonene oxide. |
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