期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 49, 页码 13414-13418出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201407088
关键词
biomimetic synthesis; cascade reactions; Diels-Alder reaction; immunosuppressants; pyrogallols
资金
- Fonds der Chemischen Industrie
- [SFB 749]
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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