Double cyclization of bis(α-hetarylmethyl)amino esters to optically active bridged N-heterocycles of HIV-inhibiting activity
Faltz H., Bender C., Wöhrl BM., Vogel-Bachmayr K., Hübscher U., Ramadan K., Liebscher J.
Anellated 1-azabicyclo[3.3.1]nonanes 6 were synthesized by several routes starting from natural α-amino esters 2 and ohaloaryl- or o-bromohetarylmethyl bromides 1. N-Alkylation of the starting amino esters to 5 and 3 was followed by halogen/lithium exchange and double cyclization. The cyclization products 6 exhibit interesting inhibition of RNase H and DNA-polymerase activity of reverse transcriptase (RT) of HIV-1 at concentrations where human cellular DNA polymerases are not affected. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.