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  • Title: Application of peptidyl radicals into a new radical cascade leading to unsaturated gamma-lactams.
    Author: Andrukiewicz R, Loska R, Prisyahnyuk V, Staliński K.
    Journal: J Org Chem; 2003 Feb 21; 68(4):1552-4. PubMed ID: 12585901.
    Abstract:
    Radical cyclization of dipeptides 1a-h proceeds smoothly to give five- and seven-membered rings in good to moderate total yields using Stork's catalytic tin hydride method. A radical is generated on a protecting group and translocated to the peptide moiety. Following a cyclization reaction, the vinyl radical can abstract hydrogen from a benzyl group on an amine, which results in elimination of the protected amine group. Encouraging results have notably been obtained with amino acids other than glycine.
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