title: Photochemical synthesis of nucleoside analogues from cyclobutanones: bicyclic and isonucleosides.
abstract: The preparation of two nucleoside analogues are reported. Both syntheses involve a key photochemical ring-expansion of cyclobutanones to an oxacarbene and its subsequent scavenging by 6-chloropurine. The synthesis of a bicyclic (locked) purine starts from a oxabicycloheptanone with a hydroxymethyl pendant. The preparation of an isonucleoside uses a cyclobutanone with an alpha-substituted 6-chloropurine. Irradiation of the latter produces an isonucleoside and acyclic nucleoside analogues.
authors.affiliation: Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M2M 4J4, Canada.
authors.forename: Mileina
authors.initials: M
authors.lastname: Jaffer
authors.forename: Abdelaziz
authors.initials: A
authors.lastname: Ebead
authors.forename: Edward
authors.initials: E
authors.lastname: Lee-Ruff
mesh_terms: D002074:Butanones / Q000737:chemistry*; D003503:Cyclobutanes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D010777:Photochemistry
chemical_list: D002074:Butanones; D003503:Cyclobutanes; D009705:Nucleosides