Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and IsonucleosidesReport as inadecuate




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Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M2M 4J4, Canada





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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 α-substituted 6-chloropurine. Irradiation of the latter produces an isonucleoside and acyclic nucleoside analogues.

Keywords: cyclobutanone; oxacarbene; bicyclic nucleosides; isonucleosides; acyclic nucleoside cyclobutanone; oxacarbene; bicyclic nucleosides; isonucleosides; acyclic nucleoside





Author: Mileina Jaffer, Abdelaziz Ebead and Edward Lee-Ruff *

Source: http://mdpi.com/



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