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Paper | Regular issue | Vol 60, No. 1, 2003, pp.57-71
Published online, 15th November, 2002
DOI: 10.3987/COM-02-9605
Synthesis of Heterocyclic γ-Amino-α,β-unsaturated Acid Derivatives and Peptide-Heterocycle Hybrids

Antonio Salgado, Enrique Mann, Francisco Sánchez-Sancho, and Bernardo Herradón*

*Instituto de Química Orgánica General, C. S. I. C., Calle Juan de Cierva, 3, 28006 Madrid, Spain

Abstract

The syntheses of the γ-amino-α,β-unsaturated esters [(R)-4, (S)-5, and (±)-6] are reported. The methodology for the preparation of these triannular heterocycles involves two synthetic sequences from N-substituted amino alcohols: a ‘one-pot’ sequential Swern oxidation-Wittig reaction and an intramolecular Heck reaction. The γ-amino-α,β-unsaturated ester [(R)-4] has been used for the synthesis of the peptide-heterocycle hybrids (19-21).