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Stereochemical investigation and total synthesis of inuloidin,a biologically active sesquiterpenoid from Heterotheca inuloides |
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| Authors: | Jumpei Kamatani Takehiro Iwadate Reiko Tajima Hideaki Kimoto Yoichi Yamada Noriyoshi Masuoka Isao Kubo Ken-ichi Nihei |
| Affiliation: | 1. Department of Applied Biochemistry, Faculty of Agriculture, Utsunomiya University, Tochigi 321-0943, Japan;2. Department of Applied Life Science, United Graduate School of Agricultural Science, Tokyo University of Agriculture and Technology, Tokyo 183-8509, Japan;3. Department of Chemistry, Faculty of Education, Utsunomiya University, Tochigi 321-0943, Japan;4. Department of Life Science, Faculty of Science, Okayama University of Science, Okayama 700-0005, Japan;5. Department of Environmental Science, Policy and Management, University of California, Berkeley, CA 94720-3114, USA |
| Abstract: | The stereochemistry of inuloidin (1), which was a sesquiterpenoid that was characterized as a plant growth inhibitory substance from Heterotheca inuloides, was investigated. The modified Mosher's method coupled with a total synthetic study using osmium oxidation and Burgess dehydration as key steps were performed to clarify the stereochemistry of 1, which was determined to be a 2S,4R isomer. |
| Keywords: | Heterotheca inuloides Sesquiterpenoid Plant growth inhibitory substance Modified Mosher's method Burgess dehydration |
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