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Synthesis and odor properties of Phantolide analogues |
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| Authors: | Masashi Kawasaki Saki Kuroyanagi Takuya Ito Hiroyuki Morita Yasuo Tanaka Naoki Toyooka |
| Institution: | 1. Department of Liberal Arts and Sciences, Faculty of Engineering, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama-ken 939-0398, Japan;2. Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan;3. Division of Natural Products Chemistry, Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan;4. Taiyo Corporation, 1-6-27 Higashiawaji, Yodogawa-ku, Osaka 533-0023, Japan;5. Graduate School of Innovation Life Science, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan |
| Abstract: | Phantolide analogues 1a–1d were newly synthesized to evaluate their odor profiles. The enantiomers of 1a and 1b were also synthesized. Both (S) enantiomers of 1a and 1b had musk odor although weakly, and but neither of the (R) enantiomers 1a and 1b had musk odor. During the investigations, we encountered the undesirable racemization in Friedel-Crafts reaction of the intermediate (S)-5. |
| Keywords: | Asymmetric synthesis Friedel-Crafts reaction Lipase Phantolide Racemization |
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