photochemical synthesis of nucleoside analogues from cyclobutanones bicyclic and isonucleosides光化学合成核苷类似物从cyclobutanones二环和isonucleosides.pdfVIP

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photochemical synthesis of nucleoside analogues from cyclobutanones bicyclic and isonucleosides光化学合成核苷类似物从cyclobutanones二环和isonucleosides.pdf

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photochemical synthesis of nucleoside analogues from cyclobutanones bicyclic and isonucleosides光化学合成核苷类似物从cyclobutanones二环和isonucleosides

Molecules 2010, 15, 3816-3828; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides Mileina Jaffer, Abdelaziz Ebead and Edward Lee-Ruff * Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M2M 4J4, Canada * Author to whom correspondence should be addressed; E-Mail: leeruff@yorku.ca; Tel.: +1-416-736-5443; Fax: +1-416-736-5936. Received: 8 April 2010; in revised form: 19 May 2010 / Accepted: 24 May 2010 / Published: 26 May 2010 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 1. Introduction Structurally modified nucleosides represent an important class of medicinal compounds which have been found to behave as therapeutic agents and are currently used in pharmaceuticals as antitumour, antiviral, and antibiotic agents [1–4]. Structural modifications include the ribose, as well as the base m