- Total synthesis of cyclotheonamide C by use of an α-keto cyanophosphorane methodology for peptide assembly
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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. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Roche, Stephane P.,Faure, Sophie,El Blidi, Lahssen,Aitken, David J.
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experimental part
p. 5067 - 5078
(2009/05/07)
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- Synthetic approaches to the southern part of cyclotheonamide C
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A synthetic equivalent of the southern segment of cyclotheonamide C, a cyclopentapeptide isolated from the sponge Theonella, has been synthesized via complementary Wadsworth-Emmons or palladium-catalysed methodologies followed by tandem oxidation/vinyloga
- Aitken, David J.,Faure, Sophie,Roche, Stéphane
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p. 8827 - 8830
(2007/10/03)
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