Total synthesis of chloptosin: A dimeric cyclohexapeptide

Oelke, Alexander J., Antonietti, Francesca, Bertone, Leonardo, Cranwell, Philippa B., France, David J., Goss, Rebecca J. M., Hofmann, Tatjana, Knauer, Stephan, Moss, Steven J., Skelton, Paul C., Turner, Richard M., Wuitschik, Georg and Ley, Steven V. (2011) Total synthesis of chloptosin: A dimeric cyclohexapeptide. Chemistry - A European Journal, 17 (15). pp. 4183-4194. ISSN 0947-6539

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Abstract

Here we describe in full our investigations into the synthesis of the dimeric cyclohexapeptide chloptosin in 17 linear steps. Particularly, this work features an organocatalytic tandem process for the synthesis of the embedded piperazic acids, in which a differentially protected azodicarboxylate is used together with pyrrolidinyl tetrazole as the catalyst. The central biaryl bond is being formed by Stille coupling of two sterically demanding ortho-chloropyrroloindole fragments. The inherent flexibility of the synthetic strategy proved beneficial as the route could be adjusted smoothly during the progression of the synthesis programme.

Item Type: Article
Uncontrolled Keywords: total,5-tetrahydropyridazine-3-carboxylic acid,cyclodepsipeptide antibiotics,(3s)-piperazic acids,cyclopeptide,asymmetric-synthesis,natural products,piperazic acid,organocatalytic route,enantioselective synthesis,organocatalysis,3,phosphorus compounds,4,quinoxapeptin a-c,(3s)-2,synthesis,vinyltriphenylphosphonium bromide,alpha-amino-acids
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Rachel Smith
Date Deposited: 16 Jun 2011 09:21
Last Modified: 19 May 2020 23:43
URI: https://ueaeprints.uea.ac.uk/id/eprint/32665
DOI: 10.1002/chem.201003216

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