Convergent access to mono-fluoroalkene-based peptidomimetics. Issue 6 (25th January 2022)

• Record Type: Journal Article
• Authors: Larnaud, Florent; Calata, Charlène; Prunier, Anaïs; Le Guen, Clothilde; Legay, Rémi; Pfund, Emmanuel; Lequeux, Thierry
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 6(2022)
• Page Start: 1205
• Page End: 1218
• Publication Date: 2022-01-25
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob02441h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Expeditive racemic synthesis of monofluoroalkene peptide isosteres from aldehydes and substituted aromatic sulfones is reported. The olefination reaction is highly Z -selective from substituted aldehydes to afford transoid peptide mimic precursors. Abstract : The convergent and selective preparation of ( Z )-monofluoroalkene-based dipeptide isosteres from functionalized fluorosulfones as a cornerstone is described. In this approach, the N -terminal amino group is introduced by a conjugate addition reaction of phthalimide onto fluorinated vinylsulfones containing α-amino-acid side chains while the C -terminal motif is linked to the fluorovinylic peptide bond mimic via the Julia–Kocienski reaction between fluorosulfones and substituted aldehydes bearing α-amino-acid side chains.