Entropically Favorable Macrolactamization. Synthesis of Isodityrosine Peptide Analogues by Tandem Erlenmeyer Condensation−Macrolactamization Karl L. Bailey Tadeusz F. Molinski 10.1021/jo9825198.s001 https://acs.figshare.com/articles/journal_contribution/Entropically_Favorable_Macrolactamization_Synthesis_of_Isodityrosine_Peptide_Analogues_by_Tandem_Erlenmeyer_Condensation_Macrolactamization/3717369 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. 1999-03-09 00:00:00 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