Total synthesis of cyclotheonamide C by use of an alpha-keto cyanophosphorane methodology for peptide assembly - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2008

Total synthesis of cyclotheonamide C by use of an alpha-keto cyanophosphorane methodology for peptide assembly

Résumé

The total synthesis of cyclotheonamide C (3), a macrocyclic pentapeptide incorporating an alpha-keto homoarginine (k-Arg) and a vinylogous dehydrotyrosine (V-deltaTyr) unit, has been achieved. For comparison of macrocyclisation feasibility, two linear pentapeptides bearing free ketone functions at the k-Arg units were prepared, by use of tandem oxidation/coupling reactions on alpha-keto cyanophosphorane precursors as the key processes for pentapeptide elaboration. Successful activation and coupling at the pentapeptide V-deltaTyr C terminus led to the target molecule core, and thus provided a short total synthesis of the target compound

Domaines

Chimie organique
Fichier principal
Vignette du fichier
EurJOC.pdf (1.77 Mo) Télécharger le fichier
Origine Fichiers produits par l'(les) auteur(s)

Dates et versions

hal-00327190 , version 1 (07-10-2008)

Identifiants

  • HAL Id : hal-00327190 , version 1

Citer

Stéphane Roche, Sophie Faure, Lahssen El Blidi, D.J. Aitken. Total synthesis of cyclotheonamide C by use of an alpha-keto cyanophosphorane methodology for peptide assembly. European Journal of Organic Chemistry, 2008, pp.5067-5078. ⟨hal-00327190⟩
154 Consultations
149 Téléchargements

Partager

Gmail Mastodon Facebook X LinkedIn More