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Stereoselective and efficient total synthesis of optically active tetrodotoxin from D-glucose |
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| Authors: | Sato Ken-ichi Akai Shoji Shoji Hirotsugu Sugita Naoki Yoshida Shiho Nagai Yoshinao Suzuki Katsuhiko Nakamura Yutaka Kajihara Yasuhiro Funabashi Masuo Yoshimura Juji |
| Institution: | Department of Applied Chemistry, Faculty of Engineering, Kanagawa University, Yokohama, 221-8686, Japan. satouk01@kanagawa-u.ac.jp |
| Abstract: | A stereoselective and efficient total synthesis of optically active tetrodotoxin (TTX) is described. A polyfunctionalized key cyclitol compound containing branched-chains for the synthesis of TTX was prepared from D-glucose employing the Henry reaction (Nitro aldol reaction) as the key transformation. Stereoselective construction of the alpha-azido-aldehyde branched-chain was achieved via the key spiro alpha-chloroepoxide intermediate. |
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