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Divergent synthesis of two precursors of 3'-homo-2'-deoxy-and 2'-homo-3'-deoxy-carbocyclic nucleosides



Divergent synthesis of two precursors of 3'-homo-2'-deoxy-and 2'-homo-3'-deoxy-carbocyclic nucleosides



Tetrahedron 58(43): 8843-8849, 21 October



Aminocyclopentanedimethanols 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. carbaldehyde. In the key step, ammonolysis of the common intermediate (+-)-(1beta,3beta,4alpha)-4-benzoyloxymethyl-1,3-cyclopentanedicarboxylic anhydride and subsequent esterification afford near-equimolar amounts of two easily separable isomeric carbomyl esters.

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Accession: 010487429

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DOI: 10.1016/s0040-4020(02)01053-0


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