Total Synthesis of Cyclotheonamide C by Use of an α-Keto Cyanophosphorane Methodology for Peptide Assembly

Journal Article

, Stéphane Roche, Sophie Faure, Lahssen El Blidi, David J. Aitken, . 2008

• Publication Work Type: Assistant Professor
• Publication Online URL: Total Synthesis of Cyclotheonamide C by Use of an α-Keto Cyanophosphorane Methodology for Peptide Assembly
• Tags: Macrocyclic peptide, α-Keto β-amino acids, α-Keto cyanophosphoranes, Total synthesis
• Magazine \ Newspaper: European Journal of Organic Chemistry
• Issue Number: 30
• Volume Number: 2008
• Pages: 5067–5078

Publication Abstract

The total synthesis of cyclotheonamide C (3), a macrocyclic pentapeptide incorporating an α-keto homoarginine (k-Arg) and a vinylogous dehydrotyrosine (V-ΔTyr) 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 α-keto cyanophosphorane precursors as the key processes for pentapeptide elaboration. Successful activation and coupling at the pentapeptide V-ΔTyr C terminus led to the target molecule core, and thus provided a short total synthesis of the target compound.