The development of a modular approach to macrocycle assembly has enabled the synthesis of a library of pyridine-based macrocyclic compds. possessing multiple donor sites where chirality was readily introduced from (R)-alanine or (S)-alanine, a representative amino acid. A facile, regioselective, nucleophilic ring opening of aziridines by dithiols enabled the synthesis of thioether-based linkers which on subsequent alkylation provided access to optically pure macrocycles. The synthesis of the target compds. was achieved by a reaction of (2S)-2-methyl-1-[(4-methylphenyl)sulfonyl]aziridine with 2,2'-(oxy)bis[ethanethiol], 2,2'-[1,2-ethanediylbis(oxy)]bis[ethanethiol], 1,3-benzenedimethanethiol. The title compds. thus formed included 3,17-dithia-6,14,23,24-tetraazatricyclo[18.104.22.168,12]tetracosa-1(23),8,10,12(24),19,21-hexaene derivs. and paracyclophane analogs.