Photochemical synthesis of nucleoside analogues from cyclobutanones: bicyclic and isonucleosides.
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.
Jaffer
Mileina
M
Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M2M 4J4, Canada.
Ebead
Abdelaziz
A
Lee-Ruff
Edward
E
D002074:Butanones / Q000737:chemistry*; D003503:Cyclobutanes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D010777:Photochemistry
D002074:Butanones; D003503:Cyclobutanes; D009705:Nucleosides