Biomimetic synthesis of the calcineurin phosphatase inhibitor dibefurin

Pascal Ellerbrock, Nicolas Armanino, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

Dibefurin is a Ci-symmetric natural product that acts as an inhibitor of calcineurin phosphatase. A six-step synthesis of this compound is reported, which features an oxidative dimerization of the aromatic polyketide epicoccine as the key step. Dibefurin is proposed to be related to epicolactone, a complex yet racemic fungal metabolite that has recently been discovered. Attempts to access epicolactone from epicoccine and epicoccone B resulted in an unusual dimer that is formed through a hetero-Diels-Alder reaction of a para-quinone methide with an ortho-quinone.

Original languageEnglish (US)
Pages (from-to)13414-13418
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number49
DOIs
StatePublished - Dec 1 2014

Keywords

  • Biomimetic synthesis
  • Cascade reactions
  • Diels-Alder reaction
  • Immunosuppressants
  • Pyrogallols

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Biomimetic synthesis of the calcineurin phosphatase inhibitor dibefurin'. Together they form a unique fingerprint.

  • Cite this