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Asymmetric synthesis of (−)-chicanine using a highly regioselective intramolecular Mitsunobu reaction and revision of its absolute configuration |
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| Authors: | Kenichi HaradaHiroki Horiuchi Kazuma TanabeRich G. Carter Tomoyuki EsumiMiwa Kubo Hideaki HiokiYoshiyasu Fukuyama |
| Affiliation: | a Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan b Department of Chemistry, Oregon State University, Gilbert Hall, Corrvallis, OR 97331, USA c Faculty of Education, Gunma University, Maebashi, Gunma 371-8510, Japan |
| Abstract: | First asymmetric synthesis of (−)-chicanine has been accomplished in 14 steps by employing the Evans asymmetric syn-selective aldol reaction, diastereoselective hydroboration and an regioselective, intramolecular Mitsunobu etherification. The absolute configuration of (+)- and (−)-chicanine has been revised to 2R,3S,4R,5R and 2S,3R,4S,5S, respectively, through CD analysis. |
| Keywords: | Talaumidin Chicanine Neolignan Neurotrophic activity Mitsunobu reaction |
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