Biomimetic Synthesis of the Calcineurin Phosphatase Inhibitor Dibefurin1. Issue 49 (4th November 2014)

• Record Type: Journal Article
• Authors: Ellerbrock, Pascal; Armanino, Nicolas; Trauner, Dirk
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 49(2014)
• Page Start: 13414
• Page End: 13418
• Publication Date: 2014-11-04
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201407088
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Dibefurin is a <italic>C_i</italic>‐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 <italic>para</italic>‐quinone methide with an <italic>ortho</italic>‐quinone.</p> </abstract>