Abstract
Boc-resin-bound alpha-hydroxy-beta-amino-aldehydes are accessible starting from N-terminally bound amino acid esters by using Dondoni's C1-homologation reaction sequence. The conversion of these synthons to two different peptide mimetics--2-hydroxy-1,3-ethyl-diamines and gamma-hydroxy-delta-amino-vinyl sulfones--has been investigated. The successful transfer of the complex alpha-amino acid homologation reaction sequence into solid-phase chemistry demonstrates the potentials of the Boc-resin for synthesis of peptidomimetics.