SYNTHESIS OF 8,1 '-ETHENO AND 8,2 '-ETHANO BRIDGED GUANOSINE DERIVATIVES USING RADICAL CYCLIZATION
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 guano...
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Published in | Heterocycles Vol. 82; no. 1; pp. 713 - 728 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier
31.12.2010
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Subjects | |
Online Access | Get more information |
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Summary: | 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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ISSN: | 0385-5414 1881-0942 |
DOI: | 10.3987/COM-10-S(E)51 |