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タイトル: Competent Route to Unsymmetric Dimer Architectures: Total Syntheses of (−)-Lycodine and (−)-Complanadines A and B, and Evaluation of Their Neurite Outgrowth Activities
著者: Zhao, Le
Tsukano, Chihiro
Kwon, Eunsang
Shirakawa, Hisashi  kyouindb  KAKEN_id
Kaneko, Shuji  kyouindb  KAKEN_id
Takemoto, Yoshiji  kyouindb  KAKEN_id
Hirama, Masahira
著者名の別形: 塚野, 千尋
白川, 久志
金子, 周司
竹本, 佳司
キーワード: C−H arylation
complanadine
lycodine
palladium
total synthesis
発行日: 18-Jan-2017
出版者: Wiley-Blackwell
誌名: Chemistry - A European Journal
巻: 23
号: 4
開始ページ: 802
終了ページ: 812
抄録: Valuable synthetic routes to the Lycopodium alkaloid lycodine (1) and its unsymmetric dimers, complanadines A (4) and B (5), have been developed. Regioselective construction of the bicyclo[3.3.1]nonane core structure of lycodine was achieved by a remote functionality‐controlled Diels–Alder reaction and subsequent intramolecular Mizoroki–Heck reaction. A key coupling reaction of the lycodine units, pyridine N‐oxide (66) and aryl bromide (65), through C−H arylation at the C1 position of 66 provided the unsymmetric dimer structure at a late stage of the synthesis. This strategy greatly simplified the construction of the dimeric architecture and functionalization. Complanadines A (4) and B (5) were synthesized by adjusting the oxidation level of the bipyridine mono‐N‐oxide (67). The diverse utility of this common intermediate (67) suggests a possible biosynthetic pathway of complanadines in Nature. Both enantiomers of lycodine (1) and complanadines A (4) and B (5) were prepared in sufficient quantities for biological evaluation. The effect on neuron differentiation of PC‐12 cells upon treatment with culture medium, in which human astrocytoma cells had been cultured in the presence of 1, 4, or 5 was evaluated.
著作権等: This is the peer reviewed version of the following article:Le Zhao, Chihiro Tsukano, Eunsang Kwon, Hisashi Shirakawa, Shuji Kaneko, Yoshiji Takemoto, Masahira Hirama, Competent Route to Unsymmetric Dimer Architectures: Total Syntheses of (−)-Lycodine and (−)-Complanadines A and B, and Evaluation of Their Neurite Outgrowth Activities, Chemistry - A European Journal, 23, 4, (802-812), (2017) which has been published in final form at https://doi.org/10.1002/chem.201604647. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
URI: http://hdl.handle.net/2433/235939
DOI(出版社版): 10.1002/chem.201604647
PubMed ID: 27758009
出現コレクション:学術雑誌掲載論文等

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