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