--------------------
- A short and novel synthesis of carbocyclic nucleosides and 4 '-epi-carbocyclic nucleosides from 2-cyclopenten-1-ones

Auteur(s): Gosselin G., Griffe L, Meillon J C, Storer R

(Article) Publié: Tetrahedron / Tetrahedron [London]; Tetrahedron Suppl; Tetrahedron (London), vol. 62 p.906-914 (2006)


Résumé:

Carbocyclic nucleoside analogues remain interesting target molecules having the potential to combine biological activity with greater metabolic stability than their sugar counterparts. This paper describes a rapid and versatile synthetic approach to such compounds based on commercial cyclopentenones (e.g., 1) that has been developed in our laboratory. Carbocyclic nucleosides like 2'-methylaristeromycin 6 were synthesized in racemic form in 5 steps via key intermediate 4. The procedure was also adapted to the preparation of 4'-epi-carbocyclic nucleosides using epoxide 17 instead of 4 and employing the same methodology. (c) 2005 Elsevier Ltd. All rights reserved.



Commentaires: 004WL Times Cited:9 Cited References Count:38