Total synthesis of exiguamines A and B inspired by catecholamine chemistry

Vladimir Sofiyev, Jean Philip Lumb, Matthew Volgraf, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

The evolution of a total synthesis of the exiguamines, two structurally unusual natural products that are highly active inhibitors of indolamine-2,3-dioxygenase (IDO), is described. The ultimately successful strategy involves advanced cross-coupling methodology and features a potentially biosynthetic tautomerization/electrocyclization cascade reaction that forms two heterocycles and installs a quaternary ammonium ion in a single synthetic operation.

Original languageEnglish (US)
Pages (from-to)4999-5005
Number of pages7
JournalChemistry - A European Journal
Volume18
Issue number16
DOIs
StatePublished - Apr 16 2012

Keywords

  • biomimetic synthesis
  • cross-coupling
  • dopamines
  • electrocyclic reactions
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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