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

Research output: Contribution to journalArticle

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

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Addition reactions
Epoxy Compounds
Renin
Nucleophiles
Imines
Chelation
Bromides
tartaric acid
cerous chloride

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

Cite this

Novel Synthesis of Three Types of C-Terminal Components of Renin Inhibitors from Unnatural (2S,3S)-Tartaric Acid. / Kobayashi, Yuko; Matsumoto, Teruyo; Takemoto, Yoshiji; Terashima, Shiro; Nakatani, Kazuhiko; Ito, Yoshio; Kamijo, Tetsuhide; Harada, Hiromu.

In: Chemical and Pharmaceutical Bulletin, Vol. 39, No. 10, 01.01.1990, p. 2550-2555.

Research output: Contribution to journalArticle

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, vol. 39, no. 10, pp. 2550-2555. https://doi.org/10.1248/cpb.39.2550
Kobayashi, Yuko ; Matsumoto, Teruyo ; Takemoto, Yoshiji ; Terashima, Shiro ; Nakatani, Kazuhiko ; Ito, Yoshio ; Kamijo, Tetsuhide ; Harada, Hiromu. / Novel Synthesis of Three Types of C-Terminal Components of Renin Inhibitors from Unnatural (2S,3S)-Tartaric Acid. In: Chemical and Pharmaceutical Bulletin. 1990 ; Vol. 39, No. 10. pp. 2550-2555.
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