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

Yuko KOBAYASHI; Teruyo MATSUMOTO; Yoshiji TAKEMOTO; Kazuhiko NAKATANI; Yoshio ITO; Tetsuhide KAMIJO; Hiromu HARADA; Shiro TERASHIMA

doi:10.1248/cpb.39.2550

Yuko KOBAYASHI, Teruyo MATSUMOTO, Yoshiji TAKEMOTO, Kazuhiko NAKATANI, Yoshio ITO, Tetsuhide KAMIJO, Hiromu HARADA, Shiro TERASHIMA

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Keywords: renin inhibitor, C-terminal component, 1, 2-amino alcohol, 1, 2, 3-amino diol, Grignard reagent, cerium(III) chloride, chelation control, oxidative cleavege, epoxide formation, epoxide opening

JOURNAL FREE ACCESS

1991 Volume 39 Issue 10 Pages 2550-2555

DOI https://doi.org/10.1248/cpb.39.2550

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Abstract

The addition reaction of cyclohexylmethylmagnesium bromide with the imine prepared from unnatural(2S, 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.

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