Toward an Asymmetric Synthesis of the Dimeric Pyranonaphthoquinone Antibiotic Crisamicin A
Toward an Asymmetric Synthesis of the Dimeric Pyranonaphthoquinone Antibiotic Crisamicin A
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DOI：
10.1021/jo501344c
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发表时间：
2014-08-01
影响因子：
3.6
通讯作者：
Sperry, Jonathan
中科院分区：
文献类型：
--
作者：
Brimble, Margaret A.;Hassan, Najmah P. S.;Sperry, Jonathan
一个完整的帐户，我们对不对称合成crisamicin A的努力。关键步骤包括氰基苯酞与手性烯酮内酯的Hauser-Kraus环化，立体选择性环化还原以安装吡喃单元，以及Suzuki homocoupling以形成关键的联芳基键。这项工作的高潮是不对称合成的二聚体轴承完整的碳骨架的二聚体吡喃萘醌天然产物crisamicin A。
A full account of our efforts toward an asymmetric synthesis of crisamicin A are presented. The key steps include a Hauser-Kraus annulation of a cyanophthalide with a chiral enone-lactone, a stereoselective cyclization-reduction to install the pyran unit, and a Suzuki homocoupling to forge the key biaryl bond. This work has culminated in the asymmetric synthesis of a dimer bearing the complete carbon skeleton of the dimeric pyranonaphthoquinone natural product crisamicin A.