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

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• 作者：Ken-ichi Sato ; Shoji Akai ; Hirotsugu Shoji ; Naoki Sugita ; Shiho Yoshida ; Yoshinao Nagai ; Katsuhiko Suzuki ; Yutaka Nakamura ; Yasuhiro Kajihara ; Masuo Funabashi ; Juji Yoshimura
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：February 15, 2008
• 年：2008
• 卷：73
• 期：4
• 页码：1234 - 1242
• 全文大小：228K
• 年卷期：v.73,no.4(February 15, 2008)
• ISSN：1520-6904

文摘

A stereoselective and efficient total synthesis of optically active tetrodotoxin (TTX) is described. Apolyfunctionalized key cyclitol compound containing branched-chains for the synthesis of TTX wasprepared from D-glucose employing the Henry reaction (Nitro aldol reaction) as the key transformation.Stereoselective construction of the -azido-aldehyde branched-chain was achieved via the key spiro-chloroepoxide intermediate.