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- Title
Biomimetic Synthesis of the Calcineurin Phosphatase Inhibitor Dibefurin.
- Authors
Ellerbrock, Pascal; Armanino, Nicolas; Trauner, Dirk
- 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.
- Subjects
BIOMIMETIC synthesis; CALCINEURIN; PHOSPHATASE inhibitors; FUNGAL metabolites; DIMERIZATION; QUINONE; CHEMICAL reactions
- Publication
Angewandte Chemie, 2014, Vol 126, Issue 49, p13632
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201407088