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

Yuko Kobayashi, Yoshio Ito, Shiro Terashima

研究成果: ジャーナルへの寄稿記事

21 引用 (Scopus)

抜粋

(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.

元の言語英語
ページ(範囲)55-66
ページ数12
ジャーナルTetrahedron
48
発行部数1
DOI
出版物ステータス出版済み - 1992
外部発表Yes

    フィンガープリント

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

これを引用