Synthesis of the ABCDG ring skeleton of communesin F based on carboborylation of 1,3-diene and Bi(OTf)3-catalyzed cyclizations
Synthesis of the ABCDG ring skeleton of communesin F based on carboborylation of 1,3-diene and Bi(OTf)3-catalyzed cyclizations
复制标题
DOI：
10.1038/s41429-019-0142-7
复制
发表时间：
2019-06-01
影响因子：
3.3
通讯作者：
Takemoto, Yoshiji
中科院分区：
文献类型：
--
作者：
Nakajima, Motoyuki;Tsukano, Chihiro;Takemoto, Yoshiji
从青霉菌(Penicillium sp.)的菌丝体中分离得到的胞外菌素是一种具有细胞毒性的七环吲哚生物碱，具有双氨基结构和两个相邻的四碳中心。在香豆素F的全合成中，我们通过1，3-二烯的碳硼化反应和Friedel-Crafts型环化反应合成了一个五环的ABCDG环骨架，并通过铋(OTf)(3)催化的S(N)2‘反应生成了氮杂环。
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)(3)-catalyzed S(N)2' reaction.