Synthesis of the ABCDG ring skeleton of communesin F based on carboborylation of 1,3-diene and Bi(OTf)(3)-catalyzed cyclizations

Nakajima Motoyuki; Tsukano Chihiro; Yasui Motohiro; Takemoto Yoshiji

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Synthesis of the ABCDG ring skeleton of communesin F based on carboborylation of 1,3-diene and Bi(OTf)(3)-catalyzed cyclizations

机译：基于1,3-二烯和Bi（OTF）（3）的Countborylation的Compyesin F的ABCDG环骨架的合成 - 催化催化

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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.

机译：与青霉菌株菌株的菌丝体分离的核心，是轴承双芳态结构和两个连续的四元碳中心的细胞毒性七型吲哚生物碱。朝着整合素F的合成，通过1,3-二烯和Friedel-Crafics型环化合成五环ABCDG环骨架，导致通过BI（OTF）（3）的氮杂环环形成 - 催化的S（n）2'反应。

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《The Journal of Antibiotics: An International Journal》 |2019年第6期|共13页
作者
Nakajima Motoyuki; Tsukano Chihiro; Yasui Motohiro; Takemoto Yoshiji;
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Kyoto Univ Grad Sch Pharmaceut Sci Sakyo Ku Kyoto 6068501 Japan;

Kyoto Univ Grad Sch Pharmaceut Sci Sakyo Ku Kyoto 6068501 Japan;

Kyoto Univ Grad Sch Pharmaceut Sci Sakyo Ku Kyoto 6068501 Japan;

Kyoto Univ Grad Sch Pharmaceut Sci Sakyo Ku Kyoto 6068501 Japan;

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正文语种 eng
中图分类药学;
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1. Synthesis of the ABCDG ring skeleton of communesin F based on carboborylation of 1,3-diene and Bi(OTf)(3)-catalyzed cyclizations [J] . Nakajima Motoyuki, Tsukano Chihiro, Yasui Motohiro, The Journal of Antibiotics: An International Journal . 2019,第6期

机译：基于1,3-二烯和Bi（OTF）（3）的Countborylation的Compyesin F的ABCDG环骨架的合成 - 催化催化
2. Synthesis of the phenanthrene and cyclohepta[ a ]naphthalene skeletons via gold(I)-catalyzed intramolecular cyclization of unactivated cyclic 5-(2-arylethyl)-1,3-dienes [J] . Yeh M.-C.P., Lin M.-N., Chou Y.-S., The Journal of Organic Chemistry . 2011,第10期

机译：通过金（I）催化未活化的环状5-（2-芳基乙基）-1,3-二烯的分子内环化反应合成菲和环庚[a]萘骨架
3. New and regioselective synthesis of 4-ylidene-tetronic acids by Lewis-acid catalyzed cyclization of 4-alkoxy-bis-(trimethylsiloxy)-1,3-diene with oxalyl chloride [J] . Langer P., Eckardt T. Synlett . 2000,第6期

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4. Highly Enantioselective Catalytic Carbon Dioxide Incorporation Reaction: Nickel-Catalyzed Asymmetric Carboxylative Cyclization of Bis-l,3-dienes [C] . Masanori Takimoto, Yoichi Nakamura, Kaoru Kimura, Symposium on Organometallic Chemistry . 2004

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5. Development of highly diastereoselective FeCl3 catalyzed prins and Friedel-Crafts cyclization and investigation of highly substituted tetrahydropyrans via Cu(OTf)2-bisphosphine olefin migration-prins cyclization. [D] . Keyes, Chad A. 2014

机译：高度非对映选择性的FeCl3催化蛋白的开发和Friedel-Crafts环化，以及通过Cu（OTf）2-双膦烯烃迁移-蛋白环化对高度取代的四氢吡喃的研究。
6. Bi(OTf)3-Catalyzed 5-Exo-Trig Cyclization via Halide Activation [O] . Ryuji Hayashi, Gregory R. Cook -1

机译：通过卤化物活化的Bi（OTf）3-催化的5-Exo-Trig环化
7. Synthesis of the ABCDG ring skeleton of communesin F based on carboborylation of 1,3-diene and Bi(OTf)3-catalyzed cyclizations [O] . Motoyuki Nakajima, Chihiro Tsukano, Motohiro Yasui, 2019

机译：基于1,3-二烯和Bi（OTF）3催化的环化的Countesin F的合成Cumeresin F的ABCDG环骨架
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机译：六氯-1,3-丁二烯与谷胱甘肽的酶促偶联。形成1-（谷胱甘肽-s-基）-1,2,3,4,4-五氯丁-1,3-二烯和1,4-双（谷胱甘肽-s-基）-1,2,3,4- tetrach lorobuta-1,3-diene。（重新公布新的可用性信息）。

Synthesis of the ABCDG ring skeleton of communesin F based on carboborylation of 1,3-diene and Bi(OTf)(3)-catalyzed cyclizations

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