@article {Manetto2007,
	title = {{Independent generation of C5 {\textquoteright}-nucleosidyl radicals in thymidine and 2 {\textquoteright}-deoxyguanosine}},
	journal = {J. Org. Chem.},
	volume = {72},
	number = {10},
	year = {2007},
	pages = {3659{\textendash}3666},
	abstract = {The synthesis of the C5{\textquoteright} tert-butyl ketone of thymidine 1a and 2{\textquoteright}-deoxyguanosine 2 is achieved by reaction of 5{\textquoteright}-C-cyano derivatives with tert-butyl lithium followed by acid hydrolysis. The 5{\textquoteright}R configuration is assigned by X-ray crystal structure determination of an opportunely protected derivative of 1a. The (5{\textquoteright}S)-isomers of both nucleosides are not stable, and a complete decomposition occurs in the reaction medium. The photochemistry of 1a and 2 effectively produced the thymidin-5{\textquoteright}-yl radical and the 2{\textquoteright}-deoxyguanosin-5{\textquoteright}-yl radical, respectively. In the thymidine system, the C5{\textquoteright} radical is fully quenched in the presence of a physiological concentration of thiols. In the 2{\textquoteright}-deoxyguanosine system, the C5{\textquoteright} radical undergoes intramolecular attack onto the C8-N7 double bond of guanine leading ultimately to the 5{\textquoteright},8-cyclo-2{\textquoteright}-deoxyguanosine derivative. The cyclization of the 2{\textquoteright}-deoxyguanosin-5{\textquoteright}-yl radical occurs with a rate constant of ca. 1 x 10(6) s(-1) and is highly stereoselective affording only the (5{\textquoteright}S)-diastereomer.},
	isbn = {0022-3263},
	doi = {10.1021/jo062518c},
	author = {Manetto, A and Georganakis, D and Leondiadis, L and Gimisis, T. and Mayer, P and Carell, T and Chatgilialoglu, C}
}
