A novel, one-pot ring expansion of cyclobutanones. Syntheses of carbovir and aristeromycin.
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.
Brown
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Department of Chemistry, Colorado State University, Fort Collins 80523, USA.
Hegedus
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LS
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D002074:Butanones / Q000138:chemical synthesis*; D015224:Dideoxynucleosides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D019380:Anti-HIV Agents; D002074:Butanones; D015224:Dideoxynucleosides; C057503:carbovir; C030034:aristeromycin; D000241:Adenosine