Synthesis 2010(5): 823-827  
DOI: 10.1055/s-0029-1218650
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of the Sugar Building Block of Bicyclo-RNA

Arben I. Haziri, Peter Silhar, Dorte Renneberg, Christian J. Leumann*
Department of Chemistry and Biochemistry, University of Bern, Freiestr. 3, 3012 Bern, Switzerland
Fax: +41(31)6313422; e-Mail: leumann@ioc.unibe.ch;
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Publikationsverlauf

Received 17 September 2009
Publikationsdatum:
25. Januar 2010 (online)

Abstract

We present the novel synthesis of two sugar units that are central intermediates for the formation of members of the bicyclo-DNA and -RNA family. The synthesis starts from commercially available 1,2:5,6-di-O-isopropylidene-α-d-glucofuranose. The key step involves the elaboration of a carbocyclic ring in a furanoside by rhodium(I)-catalyzed hydroacylation. Via this pathway, one of the sugar units is available in 8 steps and in an overall yield of 27%, while its deoxy derivative is obtained in 11 steps, which is 5 steps fewer than in our previous synthesis of this compound.