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Total Synthesis of Cordyheptapeptide A
Puentes, Alfredo R.,Neves Filho, Ricardo A. W.,Rivera, Daniel G.,Wessjohann, Ludger A.
, p. 1971 - 1974 (2017)
The first total synthesis of cordyheptapeptide A is described. The synthesis is accomplished by a convergent approach featuring a combination of peptide coupling and the Ugi reaction for the preparation of the main building blocks and the acyclic precursor. The assembly of an N-methylated fragment by the Ugi reaction comprised the utilization of a convertible isonitrile followed by activation of the C-terminal amide. Two different macrocyclization sites were evaluated, proving greater efficacy the macrolactamization at the site Ile-Tyr, likely due of a more suitable conformational bias of the acyclic precursor having an internal β-turn centered at the N -Me- d -Phe-Pro moiety.
