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Molecules 2010, 15(6), 3816-3828; doi:10.3390/molecules15063816

Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides

Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M2M 4J4, Canada
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Received: 8 April 2010 / Revised: 19 May 2010 / Accepted: 24 May 2010 / Published: 26 May 2010
(This article belongs to the Special Issue Photochemistry in Organic Synthesis)
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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
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Jaffer, M.; Ebead, A.; Lee-Ruff, E. Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides. Molecules 2010, 15, 3816-3828.

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