A novel synthesis of the 1β-methylcarbapenem key intermediate employing the [2+2]-cycloaddition reaction of chlorosulfonyl isocyanate with a 4H-1,3-dioxin derivative

Yoshio Ito, Yuko Kobayashi, Shiro Terashima

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A highly stereoselective synthetic route to the title compound was explored by featuring the [2+2]-cycloaddition reaction of chlorosulfonyl isocyanate with the 4H-1,3-dioxin derivative readily obtainable from methyl (R)-3-hydroxybutyrate, the Baeyer-Villiger reaction resulting in novel cleavage of the acetal moiety, and the Reformatsky reaction with sterically crowded 3-(2-bromopropionyl)-2-oxazolidone derivatives.

Original languageEnglish
Pages (from-to)5631-5634
Number of pages4
JournalTetrahedron Letters
Volume30
Issue number41
DOIs
Publication statusPublished - 1989
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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