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UBC Theses and Dissertations

Synthesis of potential anti-viral agents possessing the tetrahydropentaprismane ring system Tse, Hoi Lun Allan


This thesis describes the syntheses of the molecules 11-aza-pentacyclo[²՚⁷. 0⁴,⁹.0⁵, ¹⁰]decane (28) and 4,5-dimethyl-11-aza-pentacyclo [6.2.1 .0²,⁷. 0⁴,⁹.0⁵,¹⁰ ] decane (29). Owing to their structural similarities to 1-aminoadamantane (an anti-viral and anti-Parkinson's disease agent), they might possess activities against influenza viruses and/or Parkinson' disease. The key intermediates involved were the two cage ketols namely, 10-exo-hydroxytetracyclo-[²,⁶.0⁴,⁹]decan-3-one (33a) and 6,7-dimethyl-10-exo-hydroxytetracyclo [5.3.0. 0²,⁶.0⁴,⁹]decan-3-one (33b) which were prepared via a three-step sequence starting from p-benzoquinone , 1,3-butadiene and 2,3-dimethyl-1,3-butadiene respectively. The incorporation of the required nitrogen atoms was done by transforming the ketone groups of compound 33a and 33b into the corresponding oxime and oxime ether. Generation of the amine functional groups and building of the nitrogen bridges were achieved in a single step by reduction of the oxime derivatives employing aluminium hydride as the reducing agent. The syntheses of compound (28) and (29) were therefore accomplished via a five-step reaction sequence (scheme III) starting from p-benzonquinone and the corresponding butadienes.

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