A highly stereoselective synthesis of the 1β-methylcarbapenem key intermediate from (R)-3-hydroxybutyric acid

Yuko Kobayashi, Yoshio Ito, Shiro Terashima

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

(3R,4R)-4-Acetoxy-3-[(R)-1-(formyloxy)ethyl]-2-azetidinone 6 could be prepared highly stereoselectivity from (R)-3-hydroxybutyric acid by employing the [2+2]-cycloaddition reaction of chlorosulfonyl isocyanate with the 2H,4H-1,3-dioxin derivative and the Baeyer-Villiger reaction accompanying novel cleavage of the acetal moiety. The Reformatsky reaction of 6 with sterically crowded 3-(2-bromopropionyl)-2-oxazolidone derivatives readily afforded the title key intermediate after sequential chemical manipulations.

Original languageEnglish
Pages (from-to)55-66
Number of pages12
JournalTetrahedron
Volume48
Issue number1
DOIs
Publication statusPublished - Jan 1 1992
Externally publishedYes

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

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

A highly stereoselective synthesis of the 1β-methylcarbapenem key intermediate from (R)-3-hydroxybutyric acid. / Kobayashi, Yuko; Ito, Yoshio; Terashima, Shiro.

In: Tetrahedron, Vol. 48, No. 1, 01.01.1992, p. 55-66.

Research output: Contribution to journalArticle

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