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Three new optically active bis-pyridino-18-crown-6 type ligands containing four lipophilic chains at the chiral centers [(S,S,S,S)-10, (R,R,R,R)-11 and (S,S,S,S)-12] were prepared by sodium ion template effect assisted “two-to-two” type macrocyclizations. The benzyloxysubstituted (R,R,R,R)-11 and (S,S,S,S)-12 were transformed to the new pyridone analogues (R,R,R,R)-13 and (S,S,S,S)-14 by catalytic hydrogenation.

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Synthesis of new optically active bis-pyridino- and bis pyridono-18-crown-6 type ligands containing four lipophilic chains attached to the chiral centers by "two-to-two" type macrocyclization