アカイ ショウジ   Akai Shoji
  赤井 昭二
   所属   栄養学部
   職種   教授
言語種別 英語
発行・発表の年月 2005/09
形態種別 研究論文
査読 査読あり
標題 Novel and stereocontrolled synthesis of (+/-)-tetrodotoxin from myo-inositol
執筆形態 共著
掲載誌名 J. Org. Chem.
掲載区分国外
出版社・発行元 America Chemical Society Publications
巻・号・頁 70(19),pp.7496-7504
著者・共著者 K. Sato, S. Akai, N. Sugita, T. Ohsawa, T. Kogure, H. Shoji, J. Yoshimura
概要 The novel and stereocontrolled synthesis of (±)-tetrodotoxin from myo-inositol is described. The key steps involve the stepwise oxidn. of hydroxyl groups to the carbonyl function, followed by the addn. of specific nucleophiles, including the successive spiro alpha-chloro-epoxide formation and its ring- opening with the azide anion, to give the desired branched chain structures with the desired regio- and stereoselectivities in high yields. The stepwise conversion of alpha-azido aldehyde to lactone, followed by redn. of the azide, introduction of a guanidine moiety, aldehyde formation, and deprotection, produced the (±)-tetrodotoxin.