This thesis describes the syntheses of various potential inhibitors of HIV, e.g. some 3´-hydroxymethyl-substituted carbocyclic nucleoside analogues as reverse transcriptase inhibitors and some symmetry-based peptidomimetics as protease inhibitors.
Enantiomerically pure (3S,4S)-bis-(hydroxymethyl)cyclopentanone ethylene glycol ketal was used in the syntheses of eight functionalized cyclopentanol intermediates. These were either condensed with 6-chloropurine bases using the Mitsunobu reaction or converted into the corresponding cyclopentylamines, on which the purine bases were built up.
The influence of the central hydroxyl groups on the anti-viral activity of L-mannaric acid based HIV-1 protease inhibitors was investigated. L-Iditol was used as the chiral precursor in the synthesis of the inhibitors with inverted configuration at C-3 and C-4.
All target compounds described in this thesis were evaluated for anti-viral activity against the human immunodeficiency virus.
Stockholm: Stockholm University , 1999. , 54 p.