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  • Title: Solid-phase synthesis of bicyclic dipeptide mimetics by intramolecular cyclization of alcohols, thiols, amines, and amides with N-acyliminium intermediates.
    Author: Nielsen TE, Le Quement S, Meldal M.
    Journal: Org Lett; 2005 Aug 18; 7(17):3601-4. PubMed ID: 16092829.
    Abstract:
    A general strategy for the solid-phase synthesis of structurally diverse bicyclic dipeptide mimetics is presented. Depending on the amino acid side-chain (R(1)), peptide-derived N-acyliminium intermediates may undergo nucleophilic attack from either side-chain functional groups (-OH, -NH(2), -SH, and -CONH(2)) or the amide backbone (-CONH-) of the peptide, thus affording a range of aza-, thia-, and oxabicycloalkanes in excellent purity and diastereoselectivity. [reaction: see text]
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