Divergent synthesis of two precursors of 3′-homo-2′-deoxy- and 2′-homo-3′-deoxy-carbocyclic nucleosides
2002; Elsevier BV; Volume: 58; Issue: 43 Linguagem: Inglês
10.1016/s0040-4020(02)01053-0
ISSN1464-5416
AutoresJorge Blanco, Franco Fernández, Xerardo García‐Mera, José E. Rodríguez‐Borges,
Tópico(s)Biochemical and Molecular Research
ResumoAminocyclopentanedimethanols 4 and 5, which are of interest for the synthesis of higher homologues of 2′-deoxy- and 3′-deoxycarbonucleosides, respectively, were efficiently prepared by divergent routes starting from (±)-exo-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde. In the key step, ammonolysis of the common intermediate (±)-(1β,3β,4α)-4-benzoyloxymethyl-1,3-cyclopentanedicarboxylic anhydride and subsequent esterification afford near-equimolar amounts of two easily separable isomeric carbamoyl esters.
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