A novel and efficient synthesis of the key intermediate of 1β-methylcarbapenem antibiotics from (s)-methyl 3-hydroxy-2-methylpropionate

Takeo Kawabata; Yoshikazu Kimura; Yoshio Ito; Shiro Terashima; Akira Sasaki; Makoto Sunagawa

doi:10.1016/S0040-4039(00)85442-8

A novel and efficient synthesis of the key intermediate of 1β-methylcarbapenem antibiotics from (s)-methyl 3-hydroxy-2-methylpropionate

Takeo Kawabata, Yoshikazu Kimura, Yoshio Ito, Shiro Terashima, Akira Sasaki, Makoto Sunagawa

Research output: Contribution to journal › Article › peer-review

38 Citations (Scopus)

Abstract

A highly efficient synthesis of the key intermediate 2 of 1β-methylcarbapenems was accomplished in 10 steps and 30% overall yield starting from commercially available (S)-methyl 3-hydroxy-2-methylpropionate. The explored synthetic scheme features the addition reaction of diketene with a chiral imine as a key diastereoselective step.

Original language	English
Pages (from-to)	6241-6244
Number of pages	4
Journal	Tetrahedron Letters
Volume	27
Issue number	51
DOIs	https://doi.org/10.1016/S0040-4039(00)85442-8
Publication status	Published - 1986
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "A novel and efficient synthesis of the key intermediate of 1β-methylcarbapenem antibiotics from (s)-methyl 3-hydroxy-2-methylpropionate",

abstract = "A highly efficient synthesis of the key intermediate 2 of 1β-methylcarbapenems was accomplished in 10 steps and 30% overall yield starting from commercially available (S)-methyl 3-hydroxy-2-methylpropionate. The explored synthetic scheme features the addition reaction of diketene with a chiral imine as a key diastereoselective step.",

author = "Takeo Kawabata and Yoshikazu Kimura and Yoshio Ito and Shiro Terashima and Akira Sasaki and Makoto Sunagawa",

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doi = "10.1016/S0040-4039(00)85442-8",

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T1 - A novel and efficient synthesis of the key intermediate of 1β-methylcarbapenem antibiotics from (s)-methyl 3-hydroxy-2-methylpropionate

AU - Kawabata, Takeo

AU - Kimura, Yoshikazu

AU - Ito, Yoshio

AU - Terashima, Shiro

AU - Sasaki, Akira

AU - Sunagawa, Makoto

PY - 1986

Y1 - 1986

N2 - A highly efficient synthesis of the key intermediate 2 of 1β-methylcarbapenems was accomplished in 10 steps and 30% overall yield starting from commercially available (S)-methyl 3-hydroxy-2-methylpropionate. The explored synthetic scheme features the addition reaction of diketene with a chiral imine as a key diastereoselective step.

AB - A highly efficient synthesis of the key intermediate 2 of 1β-methylcarbapenems was accomplished in 10 steps and 30% overall yield starting from commercially available (S)-methyl 3-hydroxy-2-methylpropionate. The explored synthetic scheme features the addition reaction of diketene with a chiral imine as a key diastereoselective step.

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U2 - 10.1016/S0040-4039(00)85442-8

DO - 10.1016/S0040-4039(00)85442-8

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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