基于 1,3-二烯的碳硼化和 Bi(OTf)催化的环化反应合成 F 型_communesin 的 ABCDG 环骨架。
Synthesis of the ABCDG ring skeleton of communesin F based on carboborylation of 1,3-diene and Bi(OTf)-catalyzed cyclizations.
机构信息
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto, 606-8501, Japan.
出版信息
J Antibiot (Tokyo). 2019 Jun;72(6):407-419. doi: 10.1038/s41429-019-0142-7. Epub 2019 Feb 13.
Communesins, isolated from the mycelium of a strain of Penicillium sp., are cytotoxic heptacyclic indole alkaloids bearing a bis-aminal structure and two contiguous quaternary carbon centers. Toward a total synthesis of communesin F, we synthesized a pentacyclic ABCDG ring skeleton via carboborylation of 1,3-diene and a Friedel-Crafts-type cyclization, resulting in the formation of an azepine ring through a Bi(OTf)-catalyzed S2' reaction.
从一株青霉属菌株的菌丝体中分离得到的_communesin_是具有双亚胺结构和两个相邻的季碳原子的细胞毒性七环吲哚生物碱。为了实现_communesin F 的全合成，我们通过 1,3-二烯的碳硼化反应和 Frie-del-Crafts 型环化反应合成了一个五环 ABCDG 环骨架，通过 Bi(OTf)_催化的 S2'反应形成了一个氮杂环。
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