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Paper | Special issue | Vol 82, No. 1, 2010, pp.713-728
Published online, 16th July, 2010
DOI: 10.3987/COM-10-S(E)51
Synthesis of 8,1’-etheno and 8,2’-ethano Bridged Guanosine Derivatives Using Radical Cyclization

Julian Strohmeier, André Nadler, Daniel Heinrich, Ansgar Fitzner, and Ulf Diederichsen*

*Institute of Organic Chemistry, Georg-August-University, Tammannstrasse 2, D-37077 Göttingen, Germany

Abstract

Conformationally constrained nucleosides can be readily generated by radical cyclization reactions. The radical cyclization of two guanosine derivatives containing a 2,2’-dibromovinyl group or a iodovinyl group tethered at the C8 position is described, respectively. The cyclization of the guanosine derivative with the 2,2’-dibromovinyl group initiated by tributyltin hydride formed an anomeric spiro nucleoside with an 8,1’-etheno bridge as the major cyclization product. In contrast, the conversion of guanosine and 2’-deoxyguanosine derivatives carrying the iodovinyl group provided 8,2’-ethano bridged nucleosides as the major products.