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

SP Roche, S Faure, L El Blidi…

Index: Roche, Stephane P.; Faure, Sophie; El Blidi, Lahssen; Aitken, David J. European Journal of Organic Chemistry, 2008 , # 30 p. 5067 - 5078

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Citation Number: 6

Abstract

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 ...