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

Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides

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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 cyclobutanone; oxacarbene; bicyclic nucleosides; isonucleosides; acyclic nucleoside
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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