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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH FRONT

Radical Cascade Protocol for the Synthesis of (5′S)- and (5′R)-5′,8-Cyclo-2′-deoxyguanosine Derivatives*

Michael A. Terzidis A and Chryssostomos Chatgilialoglu A B

A Istituto per la Sintesi Organica e la Fotoreattività, Consiglio Nazionale delle Ricerche, Via P. Gobetti 101, 40129 Bologna, Italy.

B Corresponding author. Email: chrys@isof.cnr.it

Australian Journal of Chemistry 66(3) 330-335 http://dx.doi.org/10.1071/CH12494
Submitted: 2 November 2012  Accepted: 6 December 2012   Published: 4 February 2013

Abstract

The reaction of the appropriately substituted 8-bromo-2′-deoxyguanosine with Bu3SnH/2,2′-azobisisobutyronitrile (AIBN) can be favourably tuned to give the analogous 5′,8-cyclo-2′-deoxyguanosine derivatives in good yields, thus providing easy access to modified nucleosides that constitute an important DNA lesion. A large excess of AIBN is necessary. The creation of the new C5′–C8 bond is a non-chain radical cascade protocol.

Graphical Abstract Image


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