Bailey, Karl L. Molinski, Tadeusz F. Entropically Favorable Macrolactamization. Synthesis of Isodityrosine Peptide Analogues by Tandem Erlenmeyer Condensation−Macrolactamization Macrolactams containing a modified isodityrosine moiety were assembled by direct addition of a bis-4-aryliden-5(4<i>H</i>)-oxazolone, derived by double Erlenmeyer condensation of diaryl ether dicarboxaldehydes and an α,ω-diamine, derived from the same precursor. Tandem acylation of diamines with the bis-Erlenmeyer oxazolone gave macrolactams in yields of up to 30%. TECM demonstrates an entropically controlled 28-membered ring closure and allows rapid access to a variety of cyclic isodityrosine peptide analogues of the biologically active natural product bastadin-5. isodityrosine moiety;Macrolactam;diamine;access;variety;Entropically;diaryl ether dicarboxaldehydes;TECM;oxazolone;Tandem;Macrolactamization;Isodityrosine Peptide Analogues;bastadin;Synthesi;Condensation;entropically;bi;cyclic isodityrosine peptide analogues;tandem acylation;closure;Erlenmeyer condensation;precursor;yield;macrolactam;membered 1999-03-09
    https://acs.figshare.com/articles/journal_contribution/Entropically_Favorable_Macrolactamization_Synthesis_of_Isodityrosine_Peptide_Analogues_by_Tandem_Erlenmeyer_Condensation_Macrolactamization/3717369
10.1021/jo9825198.s001