Novel Synthesis of Three Types of C-Terminal Components of Renin Inhibitors from Unnatural (2S,3S)-Tartaric Acid

Yuko Kobayashi, Teruyo Matsumoto, Yoshiji Takemoto, Shiro Terashima, Kazuhiko Nakatani, Yoshio Ito, Tetsuhide Kamijo, Hiromu Harada

研究成果: ジャーナルへの寄稿学術誌査読

25 被引用数 (Scopus)

抄録

The addition reaction of cyclohexylmethylmagnesium bromide with the imine prepared from unnatural (2£,3S)-tartaric acid was found to proceed in a highly stereoselective manner in the presence of cerium(III) chloride. A chelation-controlled mechanism could explain the stereochemical outcome of the addition reaction. The addition product could be elaborated into three types of C-terminal components of renin inhibitors by employing oxidative cleavage of the 1,2-diol moiety, epoxide formation with inversion of configuration, and epoxide opening with a nucleophile.

本文言語英語
ページ(範囲)2550-2555
ページ数6
ジャーナルChemical and Pharmaceutical Bulletin
39
10
DOI
出版ステータス出版済み - 1990
外部発表はい

!!!All Science Journal Classification (ASJC) codes

  • 化学 (全般)
  • 創薬

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