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

doi:10.1016/S0040-4039(00)89018-8

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 › peer-review

63 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 language	English
Pages (from-to)	3031-3034
Number of pages	4
Journal	Tetrahedron Letters
Volume	31
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4039(00)89018-8
Publication status	Published - 1990
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)89018-8

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title = "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",

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.",

author = "Yuko Kobayashi and Yoshiji Takemoto and Yoshio Ito and Shiro Terashima",

year = "1990",

doi = "10.1016/S0040-4039(00)89018-8",

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journal = "Tetrahedron Letters",

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T1 - 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

AU - Kobayashi, Yuko

AU - Takemoto, Yoshiji

AU - Ito, Yoshio

AU - Terashima, Shiro

PY - 1990

Y1 - 1990

N2 - 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.

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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U2 - 10.1016/S0040-4039(00)89018-8

DO - 10.1016/S0040-4039(00)89018-8

M3 - Article

AN - SCOPUS:0025357897

VL - 31

SP - 3031

EP - 3034

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 21

ER -

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

Abstract

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