Diastereofacial Selective Addition of Ethynylcerium Reagent and Barton−McCombie Reaction as the Key Steps for the Synthesis of C-3‘-Ethynylribonucleosides and of C-3‘-Ethynyl-2‘-deoxyribonucleosides
- 1 November 1997
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 62 (24) , 8309-8314
- https://doi.org/10.1021/jo9704568
Abstract
We describe the preparation of 3'-alkynyluridine 4a and -adenosine 4b and of 3'-alkynyl-2'-deoxyuridine 16a and -adenosine 16b starting from the corresponding nucleosides. The desired stereochemistry of the C-3' tertiary alcohol was obtained by reaction of an ethynylcerium-lithium reagent on a 3'-ketonucleoside with the hydroxyl group at C-5' unprotected. The 2'-deoxygenation was performed by a Barton-McCombie reaction under appropriate conditions where the addition of tin hydride to the triple bond was suppressed. Evaluation of the anti-HIV activity of the C-3' modified nucleosides is reported.Keywords
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