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Volume 82, Issue 1
Received, 9th June, 2010, Accepted, 15th July, 2010, Published online, 16th July, 2010. |
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| 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 |
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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. |
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Graphical Abstract
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| Corresponding author; email: udieder@gwdg.de |
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