Biomimetic Synthesis of the Calcineurin Phosphatase Inhibitor Dibefurin
Biomimetic Synthesis of the Calcineurin Phosphatase Inhibitor Dibefurin
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DOI：
10.1002/anie.201407088
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发表时间：
2014-12-01
影响因子：
16.6
通讯作者：
Trauner, Dirk
中科院分区：
文献类型：
--
作者：
Ellerbrock, Pascal;Armanino, Nicolas;Trauner, Dirk
Dibefurin是一种C1-对称的天然产物，可作为钙调磷酸酶的抑制剂。报道了该化合物的六步合成法，其特征在于芳香族聚酮epicocine的氧化二聚反应是关键步骤。地贝福林被认为与epicolactone有关，epicolactone是最近发现的一种复杂的外消旋真菌代谢物。尝试从epicoccine和epicoccone B中获得epicolactone导致了一种不寻常的二聚体，该二聚体是通过对醌甲基化物与邻醌的异Diels-桤木反应形成的。
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.