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

研究成果: ジャーナルへの寄稿 › 記事

62 引用 (Scopus)

抄録

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.

元の言語英語
ページ（範囲）3031-3034
ページ数4
ジャーナルTetrahedron Letters
巻31
発行部数21
DOI
出版物ステータス出版済み - 1990
外部発表Yes

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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

これを引用

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.

：: Tetrahedron Letters, 巻 31, 番号 21, 1990, p. 3031-3034.

研究成果: ジャーナルへの寄稿 › 記事

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, 巻. 31, 番号 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. ：: Tetrahedron Letters. 1990 ; 巻 31, 番号 21. pp. 3031-3034.
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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.",
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AU - Ito, Yoshio

AU - Terashima, Shiro

PY - 1990

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AB - 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.

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