Synthesis of Monofluoro Building Blocks Designed from Fine Chemistry Viewpoint and Development of Fluorine-containing Medicinals

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1) Among the various monofluoro building blocks designed, 1-6, synthesis of the four compounds 1-4 was achieved. However, the isolation of the selenenyl derivative 5 and the fluoroethene equivalent 6 was unsuccessful due to the instability caused by the multifunctional carbon structures.2) Synthesis of the chiral tropane precursors, 7 and 8, was achieved. However. further efforts to convert them into chiral tropanes was abandoned because this pathway involves some reactions with unsatisfactory yields.3) As to the development of the general entry to the novel tertiary alkyl fluorides, we succeeded to get to the target structure 13 by two routes, i. e., the alkylation of 11 obtained from 9 via 10 and the alkylation of 12 obtained from 9.4) The synthesis of various precursors for alpha-fluoro-alpha-amino acids, including 15 and 16, has been achieved. However, the target compounds could not be isolated due to the rather drastic reaction conditions employed for the final stage and also to the instability of the target compounds.5) Four compounds 14-17 were tested for fencyclidine inhibitory activity and monofluorotropane 18 was tested for nicotinic activity. However, all of them were found to be not so effective as we had expected.