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...

Full description

Saved in:
Bibliographic Details
Published inHeterocycles Vol. 82; no. 1; pp. 713 - 728
Main Authors Strohmeier, Julian, Nadler, Andre, Heinrich, Daniel, Fitzner, Ansgar, Diederichsen, Ulf
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 31.12.2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SECONDARY ALCOHOLS
OXIDATION
Nucleosidation
CONVERSION
Radical Cyclization
SIMPLIFIED NUCLEOSIDE SYNTHESIS
ANOMERIC SPIRO NUCLEOSIDES
DNA
Nucleoside
Z-DNA
Conformation
BASE
Online AccessGet more information

Cover

More Information
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.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-10-S(E)51