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

Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides

Mileina Jaffer, Abdelaziz Ebead and Edward Lee-Ruff* email
Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M2M 4J4, Canada
* Author to whom correspondence should be addressed.
Received: 8 April 2010; in revised form: 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

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Cite This Article

MDPI and ACS Style

Jaffer, M.; Ebead, A.; Lee-Ruff, E. Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides. Molecules 2010, 15, 3816-3828.

AMA Style

Jaffer M, Ebead A, Lee-Ruff E. Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides. Molecules. 2010; 15(6):3816-3828.

Chicago/Turabian Style

Jaffer, Mileina; Ebead, Abdelaziz; Lee-Ruff, Edward. 2010. "Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides." Molecules 15, no. 6: 3816-3828.

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