Templated scaffolds of cis-and trans-tetrahydrofuran gamma-amino acids: gamma-azido-beta-hydroxy-tetrahydrofuran-2-carboxylates from pentono-delta-lactones

摘要

Short syntheses of enantiomeric templated scaffolds to cis-and trans-tetrahydrofuran gamma-amino acids from pentono-delta-lactones derived from arabinose and ribose are reported; an unexpectedly efficient synthesis of a templated tetrahydrofuran beta-amino acid by azide displacement of a triflate beta to an ester function proceeds with remarkably little elimination. These materials should allow evaluation of such peptidomimetics to induce predisposition towards secondary structurs.