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

Fingerprint

Oxazolidinones
Acetals
Dioxins
3-Hydroxybutyric Acid
Cycloaddition
Cycloaddition Reaction
Derivatives
1 beta-methylcarbapenem
chlorosulfonyl isocyanate

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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. / Ito, Yoshio; Kobayashi, Yuko; Terashima, Shiro.

In: Tetrahedron Letters, Vol. 30, No. 41, 1989, p. 5631-5634.

Research output: Contribution to journalArticle

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