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

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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 languageEnglish
Pages (from-to)6241-6244
Number of pages4
JournalTetrahedron Letters
Volume27
Issue number51
DOIs
Publication statusPublished - 1986
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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