Total Synthesis of Chloptosin: A Dimeric Cyclohexapeptide

Alexander J. Oelke, Francesca Antonietti, Leonardo Bertone, Philippa B. Cranwell, David J. France, Rebecca J. M. Goss, Tatjana Hofmann, Stephan Knauer, Steven J. Moss, Paul C. Skelton, Richard M. Turner, Georg Wuitschik, Steven V. Ley*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4183-4194
Number of pages12
JournalChemistry - A European Journal
Volume17
Issue number15
DOIs
Publication statusPublished - Apr 2011

Keywords

  • CYCLODEPSIPEPTIDE ANTIBIOTICS
  • (3S)-PIPERAZIC ACIDS
  • cyclopeptide
  • ASYMMETRIC-SYNTHESIS
  • natural products
  • piperazic acid
  • ORGANOCATALYTIC ROUTE
  • ENANTIOSELECTIVE SYNTHESIS
  • total synthesis
  • organocatalysis
  • (3S)-2,3,4,5-TETRAHYDROPYRIDAZINE-3-CARBOXYLIC ACID
  • PHOSPHORUS COMPOUNDS
  • QUINOXAPEPTIN A-C
  • ALPHA-AMINO-ACIDS
  • VINYLTRIPHENYLPHOSPHONIUM BROMIDE

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