A stereoselective synthesis of the (2R, 3S)- and (2S, 3R)-3-amino-2-hydroxybutyric acid derivatives, the key components of a renin inhibitor and bestatin.

Yuko Kobayashi, Yoshiji Takemoto, Tetsuhide Kamijo, Hiromu Harada, Yoshio Ito, Shiro Terashima

Research output: Contribution to journalArticle

68 Citations (Scopus)

Abstract

The title synthesis was achieved by featuring the [2+2]-cycloaddition reaction of benzyloxyketene with a chiral imine derived from methyl (R)- or (S)-mandelate, alcoholysis of the formed 3,4-cis disubstituted β-lactam under acidic conditions, and reductive removal obtained by the [2+2]-cycloaddition reaction employing achiral and chiral imines derived from benzylamine, p-anisidine, di-panisylmethylamine, and (S)-l-phenylethylamine were also reported. Stereoselectivity of the [2+2]-cycloaddition reaction could be explained by the initial formation of a zwitter-ionic intermediate and its subsequent conrotatory ring closure.

Original languageEnglish
Pages (from-to)1853-1868
Number of pages16
JournalTetrahedron
Volume48
Issue number10
DOIs
Publication statusPublished - Jan 1 1992
Externally publishedYes

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Hydroxybutyrates
Cycloaddition
Cycloaddition Reaction
Renin
Imines
Phenethylamines
Stereoselectivity
Lactams
3-amino-2-hydroxybutanoic acid
ubenimex

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

A stereoselective synthesis of the (2R, 3S)- and (2S, 3R)-3-amino-2-hydroxybutyric acid derivatives, the key components of a renin inhibitor and bestatin. / Kobayashi, Yuko; Takemoto, Yoshiji; Kamijo, Tetsuhide; Harada, Hiromu; Ito, Yoshio; Terashima, Shiro.

In: Tetrahedron, Vol. 48, No. 10, 01.01.1992, p. 1853-1868.

Research output: Contribution to journalArticle

Kobayashi, Yuko ; Takemoto, Yoshiji ; Kamijo, Tetsuhide ; Harada, Hiromu ; Ito, Yoshio ; Terashima, Shiro. / A stereoselective synthesis of the (2R, 3S)- and (2S, 3R)-3-amino-2-hydroxybutyric acid derivatives, the key components of a renin inhibitor and bestatin. In: Tetrahedron. 1992 ; Vol. 48, No. 10. pp. 1853-1868.
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AU - Ito, Yoshio

AU - Terashima, Shiro

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