Sato Ken-ichi, Akai Shoji, Shoji Hirotsugu, Sugita Naoki, Yoshida Shiho, Nagai Yoshinao, Suzuki Katsuhiko, Nakamura Yutaka, Kajihara Yasuhiro, Funabashi Masuo, Yoshimura Juji
Department of Applied Chemistry, Faculty of Engineering, Kanagawa University, Yokohama, 221-8686, Japan.
J Org Chem. 2008 Feb 15;73(4):1234-42. doi: 10.1021/jo701655v. Epub 2008 Jan 19.
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.
描述了一种对映体选择性且高效的光学活性河豚毒素（TTX）的全合成方法。采用亨利反应（硝基醛醇反应）作为关键转化步骤，由D-葡萄糖制备了一种用于合成TTX的含支链的多官能团关键环糖醇化合物。通过关键的螺α-氯环氧中间体实现了α-叠氮基醛支链的立体选择性构建。
