- Divergent synthesis of two precursors of 3′-homo-2′-deoxy- and 2′-homo-3′-deoxy-carbocyclic nucleosides
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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. 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.
- Blanco, José M,Fernández, Franco,García-Mera, Xerardo,Rodríguez-Borges, José E
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p. 8843 - 8849
(2007/10/03)
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- SYNTHESIS OF RING-ENLARGED CYCLOBUT-A AND CYCLOBUT-G ANALOGUES AS HIV INHIBITORS. PART 4
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Two ring-expanded analogues (compounds 13 and 14) of the anti-HIV agents Cyclobut-A and Cyclobut-G are described.They were synthesized from trans-3,4-bis(hydroxymethyl)cyclobutylamine which was obtained from threo-3,4-bis(methoxycarbonyl)hexane dioic acid.Neither compound (13,14) was able to provide protection to CEM cells against HIV-1-infection.
- Boumchita, Hassane,Legraverend, Michel,Bisagni, Emile
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p. 1785 - 1792
(2007/10/02)
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