Total synthesis of (-)-5,6,11-trideoxytetrodotoxin and its 4-epimer |
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| Authors: | Umezawa Taiki Hayashi Toshihiro Sakai Hiroshi Teramoto Hidetoshi Yoshikawa Takeshi Izumida Masashi Tamatani Yoshinori Hirose Tadashi Ohfune Yasufumi Shinada Tetsuro |
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| Institution: | Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan. |
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| Abstract: | reaction: see text] The first total synthesis of 5,6,11-trideoxytetrodotoxin (1) and its 4-epimer were achieved. The synthesis is characterized by the stereoselective construction of the quaternary amino carbon center at C8a by an asymmetric transferring Strecker synthesis and the highly efficient conversion of cyanohydrin 4 to 1 via intramolecular cyclization reactions. |
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