A novel synthesis of the (2R,3S)- and (2S3R)-3-amino-2-hydroxycarboxylic acid derivatives, the key components of a renin inhibitor and bestatin, from methyl (R)- and (S-mandelate

Yuko Kobayashi, Yoshiji Takemoto, Yoshio Ito, Shiro Terashima

Research output: Contribution to journal › Article

62 Citations (Scopus)

Abstract

The title synthesis could be accomplished by featuring the [2+2]-cycloaddition reaction of a chiral imine with benzyloxyketene, alcoholysis of the formed 2-azetidinone derivative, and reductive removal of the mandelate-derived benzylic oxygen by way of a 2-oxazolidone derivative.

Original languageEnglish
Pages (from-to)3031-3034
Number of pages4
JournalTetrahedron Letters
Volume31
Issue number21
DOIs
Publication statusPublished - 1990
Externally publishedYes

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Oxazolidinones
Imines
Cycloaddition Reaction
Renin
Oxygen
Derivatives
Acids
Cycloaddition
ubenimex
2-azetidinone

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

A novel synthesis of the (2R,3S)- and (2S3R)-3-amino-2-hydroxycarboxylic acid derivatives, the key components of a renin inhibitor and bestatin, from methyl (R)- and (S-mandelate. / Kobayashi, Yuko; Takemoto, Yoshiji; Ito, Yoshio; Terashima, Shiro.

In: Tetrahedron Letters, Vol. 31, No. 21, 1990, p. 3031-3034.

Research output: Contribution to journal › Article

Kobayashi, Y, Takemoto, Y, Ito, Y & Terashima, S 1990, 'A novel synthesis of the (2R,3S)- and (2S3R)-3-amino-2-hydroxycarboxylic acid derivatives, the key components of a renin inhibitor and bestatin, from methyl (R)- and (S-mandelate', Tetrahedron Letters, vol. 31, no. 21, pp. 3031-3034. https://doi.org/10.1016/S0040-4039(00)89018-8
Kobayashi Y, Takemoto Y, Ito Y, Terashima S. A novel synthesis of the (2R,3S)- and (2S3R)-3-amino-2-hydroxycarboxylic acid derivatives, the key components of a renin inhibitor and bestatin, from methyl (R)- and (S-mandelate. Tetrahedron Letters. 1990;31(21):3031-3034. https://doi.org/10.1016/S0040-4039(00)89018-8
Kobayashi, Yuko ; Takemoto, Yoshiji ; Ito, Yoshio ; Terashima, Shiro. / A novel synthesis of the (2R,3S)- and (2S3R)-3-amino-2-hydroxycarboxylic acid derivatives, the key components of a renin inhibitor and bestatin, from methyl (R)- and (S-mandelate. In: Tetrahedron Letters. 1990 ; Vol. 31, No. 21. pp. 3031-3034.
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