Biomimetic synthesis of the calcineurin phosphatase inhibitor dibefurin

Pascal Ellerbrock; Nicolas Armanino; Dirk Trauner

doi:10.1002/anie.201407088

Biomimetic synthesis of the calcineurin phosphatase inhibitor dibefurin

Pascal Ellerbrock, Nicolas Armanino, Dirk Trauner

Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	13414-13418
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	49
DOIs	https://doi.org/10.1002/anie.201407088
State	Published - Dec 1 2014

Keywords

Biomimetic synthesis
Cascade reactions
Diels-Alder reaction
Immunosuppressants
Pyrogallols

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201407088

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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.",

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Biomimetic synthesis of the calcineurin phosphatase inhibitor dibefurin

Abstract

Keywords

ASJC Scopus subject areas

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