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

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24 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2550-2555
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume39
Issue number10
DOIs
Publication statusPublished - Jan 1 1990
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

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    Kobayashi, Y., Matsumoto, T., Takemoto, Y., Terashima, S., Nakatani, K., Ito, Y., Kamijo, T., & Harada, H. (1990). Novel Synthesis of Three Types of C-Terminal Components of Renin Inhibitors from Unnatural (2S,3S)-Tartaric Acid. Chemical and Pharmaceutical Bulletin, 39(10), 2550-2555. https://doi.org/10.1248/cpb.39.2550