%0 Journal Article
%T Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides
%A Mileina Jaffer
%A Abdelaziz Ebead
%A Edward Lee-Ruff
%J Molecules
%D 2010
%I MDPI AG
%R 10.3390/molecules15063816
%X 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 ¦Á-substituted 6-chloropurine. Irradiation of the latter produces an isonucleoside and acyclic nucleoside analogues.
%K cyclobutanone
%K oxacarbene
%K bicyclic nucleosides
%K isonucleosides
%K acyclic nucleoside
%U http://www.mdpi.com/1420-3049/15/6/3816