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A novel total synthesis of isocryptolepine based on a microwave-assisted tandem Curtius rearrangement and aza-electrocyclic reaction |
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| Authors: | Kaori Hayashi Tominari Choshi Kyoko Chikaraishi Aimi Oda Rikako Yoshinaga Noriyuki Hatae Minoru Ishikura Satoshi Hibino |
| Institution: | 1. Graduate School of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama, Hiroshima 729-0292, Japan;2. Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama, Ehime 790-8578, Japan;3. Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan |
| Abstract: | A new entry to the total synthesis of isocryptolepine (cryptosanguinolentine), isolated from Cryptolepis sanguinolenta, was achieved by constructing a tetracyclic ring system through a microwave-assisted tandem Curtius rearrangement and electrocyclic reaction of an aza 6π-electron system. The tetracyclic lactam was converted to isocryptolepine in a four-step sequence. |
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