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Synlett 1990; 1990(1): 58-63
DOI: 10.1055/s-1990-20989
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Synthesis and Chemical Resolution of a Novel Class of Rigid 1-(1-Phenylcyclohexyl)-iperidine(PCP) Analogues

Alan P. Kozikowski* , Yuan-Ping Pang
  • *Departments of Chemistry and Behavioral Neuroscience, University of Pittsburgh, Chevron Science Center, Pittsburgh, PA 15260, USA
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Publication Date:
08 March 2002 (online)

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A novel class of conformationally rigidified phencyclidine (1-(1-phenylcyclohexyl)piperidine; PCP) analogues -4a-amino-1,4,4a,9a-tetrahydrofluorenes 1, 2, 5, 6 and 4a-amino-1,2,3,4,4a,9a-hexahydrofluorenes 3, 4, 7, 8 - has been prepared through a Diels-Alder approach and resolved by aid of (+)- and (-)-tartaric acid. One member of this series, the (4aR, 9aS)-4a-amino derivative 3, was found to exhibit a high affinity (IC50 = 19 nm) for the PCP recognition site in the brain, thus allowing a more rigorous assignment of the conformation of PCP relevant to binding at these sites.