Total Synthesis of cis-Clavicipitic Acid from Asparagine via Ir-Catalyzed C-H bond Activation as a Key Step

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Abstract

4-Substituted tryptophan derivatives and the total synthesis of cis-clavicipitic acid were achieved in reactions in which Ir-catalyzed C-H bond activation was a key step. The starting material for these reactions is asparagine, which is a cheap natural amino acid. The reductive amination step from the 4-substituted tryptophan derivative gave cis-clavicipitic acid with perfect diastereoselectivity.

Original languageEnglish
Pages (from-to)11340-11343
Number of pages4
JournalChemistry (Weinheim an der Bergstrasse, Germany)
Volume21
Issue number32
DOIs
Publication statusPublished - 2015 Aug 3

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Keywords

  • 4-substituted tryptophan derivatives
  • clavicipitic acid
  • CH activation
  • iridium
  • total synthesis

ASJC Scopus subject areas

  • Medicine(all)

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