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

Fingerprint

Dimerization
Phosphatases
Biomimetics
Metabolites
Dimers
Polyketides
Biological Products
dibefurin
calcineurin phosphatase
quinone methide
benzoquinone

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Biomimetic synthesis of the calcineurin phosphatase inhibitor dibefurin. / Ellerbrock, Pascal; Armanino, Nicolas; Trauner, Dirk.

In: Angewandte Chemie - International Edition, Vol. 53, No. 49, 01.12.2014, p. 13414-13418.

Research output: Contribution to journalArticle

Ellerbrock, Pascal ; Armanino, Nicolas ; Trauner, Dirk. / Biomimetic synthesis of the calcineurin phosphatase inhibitor dibefurin. In: Angewandte Chemie - International Edition. 2014 ; Vol. 53, No. 49. pp. 13414-13418.
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