A. B. Smith, III et
al.60 constructed a novalpeptide scaffold for β-strand/sheet and
related secondary peptide structural mimics are described. The scaffold,
consisting of a repeating array of 2, 5, 5-trisubsttuted pyrrolinone
(enaminone) units punctuated with appropriate amino side chains, is
conceptually related to their previously successful 3, 5-linked polypyrrolinone
non-peptidepeptidomimetic scaffold. Construction of the 2, 5, 5-trisubstituted
pyrrolinone ring system proceeds via intramolecular condensation of an
N-protected amino dione. The latter is prepared from a protected α-amino ketons
and aldehyde via an aldol-oxidation reaction sequence as shown in scheme 23.
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60. A. B. Smith, III, S. T. Knight, P. A. Sprengeler, and R. Hirschmann Bioorg. Med. Chem., 1996, 4, 1021.
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