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

Y Kobayashi, Y Ito, S Terashima

Index: Kobayashi, Yuko; Ito, Yoshio; Terashima, Shiro Tetrahedron, 1992 ,  vol. 48,  # 1  p. 55 - 66

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Citation Number: 29

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 ...