The Journal of organic chemistry

A novel, one-pot ring expansion of cyclobutanones. Syntheses of carbovir and aristeromycin

B Brown, LS Hegedus

Index: Brown, Brian; Hegedus, Louis S. Journal of Organic Chemistry, 2000 , vol. 65, # 6 p. 1865 - 1872

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Citation Number: 62

Abstract

A novel, one-pot ring-expansion procedure was developed using Me3S (O) I, NaH, and Sc (OTf) 3. The scope and limitations were briefly examined, and a tentative mechanism was proposed. Application of the methodology to known cyclobutanone 1 provided the corresponding cyclopentanone, which was successfully advanced to (+)-carbovir and (+)- aristeromycin.