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Stereoselective and Efficient Total Synthesis of Optically Active Tetrodotoxin from d-Glucose

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journal contribution
posted on 15.02.2008, 00:00 by Ken-ichi Sato, Shoji Akai, Hirotsugu Shoji, Naoki Sugita, Shiho Yoshida, Yoshinao Nagai, Katsuhiko Suzuki, Yutaka Nakamura, Yasuhiro Kajihara, Masuo Funabashi, Juji Yoshimura
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 α-azido-aldehyde branched-chain was achieved via the key spiro α-chloroepoxide intermediate.