Tetrahedron Letters

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

Y Ito, Y Kobayashi, S Terashima

Index: Ito, Yoshio; Kobayashi, Yuko; Terashima, Shiro Tetrahedron Letters, 1989 ,  vol. 30,  # 41  p. 5631 - 5634

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Citation Number: 5

Abstract

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.