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Synthesis of new nucleoside analogues comprising a methylenecyclobutane unit |
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| Authors: | Sophie Danappe,Christian Alexandre,Anne-Marie Aubertin,Franç ois Huet |
| Affiliation: | a Laboratoire de Synthèse Organique, UMR CNRS 6011, Faculté des Sciences, Université du Maine, Avenue Olivier Messiaen, F-72085 Le Mans Cedex 9, France b Institut de Virologie, INSERM U 544, Faculté de Médecine, Université Louis Pasteur, 3 Rue Koeberlé, F-67000 Strasbourg, France c Laboratoire de Biologie et Chimie Moléculaires, Centre de recherche et d'enseignement Yves Coppens, Campus de Tohannic, BP 573, F-56017 Vannes, France |
| Abstract: | Synthesis of eight nucleoside analogues 3-10 with a methylene cyclobutane unit is described. Wittig or Peterson reactions with protected 2-hydroxycyclobutanones 12 and 13 gave E- and Z-derivatives, respectively. After functional modifications the heterocyclic moieties were introduced via a Mitsunobu reaction either on the lateral chain or on the cycle. When adenine was used in this reaction only the N-9 substitution products were obtained. Removal of the protecting groups provided the target products. |
| Keywords: | Nucleoside analogues Methylenecyclobutane Mistsunobu conditions |
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