The catalytic modification of the Sharplessepoxidation reaction was employed in a short EPC-synthesis of the title compound. The asymmetric epoxidation of the allylic alcohol (6) proceeded in 75 % yield and 94 % enantiomeric excess. In a 4 step sequence the epoxide (7) was transformed to (S)-3-hydroxy-3-mercaptomethylquinuclidine (11).
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Resolution of (RS)-tetrindole (3) and enantioselective reductions of the imine 7 yielded (S)-(+)-(4) and (R)-(-)-tetrindole (5). The absolute stereochemistry of 4 was established by X-ray analysis of the corresponding Mosher amide 6. From in vitro as well as in vivo data (MAO-inhibition, levels of monoamines and their respective metabolites in rat brain), 4 was identified as the eutomer.
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