Novel applications of convertible isonitriles for the synthesis of mono and bicyclic γ-lactams via a UDC strategy

Christopher Hulme, Liang Ma, Marie Pierre Cherrier, Joseph J. Romano, George Morton, Celine Duquenne, Joseph Salvino, Richard Labaudiniere

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Abstract

This communication reveals a novel application of the so-called convertible isonitriles for the solution/solid phase generation of γ-lactam analogues. Use of tethered N-BOC aldehydes in the Ugi multi-component reaction (MCR), followed by BOC removal and base treatment (a '3-step, 1-pot procedure') affords γ-lactams in good yield. The UDC (Ugi/De-BOC/Cyclize) strategy, coupled with a convertible isonitrile, is now feasible from all three substitution sites of the Ugi product. A conceptually novel approach, combining a bi-functional precursor with a post-condensation modification to give fused lactam-ketopiperazines, is also revealed.

Original languageEnglish (US)
Pages (from-to)1883-1887
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number12
DOIs
StatePublished - Mar 18 2000
Externally publishedYes

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Hulme, C., Ma, L., Cherrier, M. P., Romano, J. J., Morton, G., Duquenne, C., Salvino, J., & Labaudiniere, R. (2000). Novel applications of convertible isonitriles for the synthesis of mono and bicyclic γ-lactams via a UDC strategy. Tetrahedron Letters, 41(12), 1883-1887. https://doi.org/10.1016/S0040-4039(00)00052-6