title: A novel, one-pot ring expansion of cyclobutanones. Syntheses of carbovir and aristeromycin.
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.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins 80523, USA.
authors.forename: B
authors.initials: B
authors.lastname: Brown
authors.forename: L S
authors.initials: LS
authors.lastname: Hegedus
mesh_terms: 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
chemical_list: D019380:Anti-HIV Agents; D002074:Butanones; D015224:Dideoxynucleosides; C057503:carbovir; C030034:aristeromycin; D000241:Adenosine