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5-Aminooxazole as an Internal Traceless Activator of C-Terminal Carboxylic Acid: Rapid Access to Diversely Functionalized Cyclodepsipeptides

Bughin, Carine ; Zhao, Gang ; Bienaymé, Hugues ; Zhu, Jieping

Chemistry : a European journal, 2006-01, Vol.12 (4), p.1174-1184 [Periódico revisado por pares]

Weinheim: WILEY-VCH Verlag

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  • Título:
    5-Aminooxazole as an Internal Traceless Activator of C-Terminal Carboxylic Acid: Rapid Access to Diversely Functionalized Cyclodepsipeptides
  • Autor: Bughin, Carine ; Zhao, Gang ; Bienaymé, Hugues ; Zhu, Jieping
  • Assuntos: Carboxylic Acids - chemistry ; Chemical Sciences ; Cyclization ; Depsipeptides - chemical synthesis ; domino reactions ; macrocycles ; multicomponent reactions ; Organic chemistry ; Oxazoles - chemistry ; peptides ; Spironolactone - chemistry ; Trifluoroacetic Acid - chemistry
  • É parte de: Chemistry : a European journal, 2006-01, Vol.12 (4), p.1174-1184
  • Notas: istex:C09FA87B0F1C7C423A9B5D851E396BF7D116988F
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    ArticleID:CHEM200500703
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  • Descrição: A conceptually novel macrolactonization protocol has been developed. It is a domino process involving a sequence of: 1) protonation of 5‐aminooxazole leading to the electrophilic iminium salt; 2) trapping of the iminium species by the neighboring C‐terminal carboxylic acid leading to a putative spirolactone; and 3) intramolecular nucleophilic addition of the tethered alcohol to the spirolactone followed by fragmentation. The strategically incorporated 5‐aminooxazole serves as an internal traceless activator of the neighboring C‐terminal carboxylic acid, since it became an integral part of the peptide backbone after cyclization. No coupling reagent is required and the entire sequence is triggered by just a few equivalents of trifluoroacetic acid under very mild conditions (MeCN as the solvent at room temperature). The spirolactone as an activated form of the carboxylic acid has been evidenced by a sulfur‐migration experiment. By combining with a three‐component synthesis of 5‐aminooxazole, a two‐step synthesis of structurally complex cyclodepsipeptides from readily accessible starting materials was developed. A conceptually novel macrolactonization protocol using 5‐aminooxazole as an internal traceless activator of a neighboring carboxylic acid has been developed. Its combination with a three‐component synthesis of oxazole leads to a two‐step synthesis of complex cyclodepsipeptides from readily accessible starting materials (see scheme).
  • Editor: Weinheim: WILEY-VCH Verlag
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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