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dc.contributor.author | Zhao, Le | en |
dc.contributor.author | Tsukano, Chihiro | en |
dc.contributor.author | Kwon, Eunsang | en |
dc.contributor.author | Shirakawa, Hisashi | en |
dc.contributor.author | Kaneko, Shuji | en |
dc.contributor.author | Takemoto, Yoshiji | en |
dc.contributor.author | Hirama, Masahira | en |
dc.contributor.alternative | 塚野, 千尋 | ja |
dc.contributor.alternative | 白川, 久志 | ja |
dc.contributor.alternative | 金子, 周司 | ja |
dc.contributor.alternative | 竹本, 佳司 | ja |
dc.date.accessioned | 2019-01-07T04:59:27Z | - |
dc.date.available | 2019-01-07T04:59:27Z | - |
dc.date.issued | 2017-01-18 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | http://hdl.handle.net/2433/235939 | - |
dc.description.abstract | 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. | en |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | Wiley | en |
dc.rights | 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. | en |
dc.rights | This is not the published version. Please cite only the published version. | en |
dc.rights | 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。 | ja |
dc.subject | C−H arylation | en |
dc.subject | complanadine | en |
dc.subject | lycodine | en |
dc.subject | palladium | en |
dc.subject | total synthesis | en |
dc.title | Competent Route to Unsymmetric Dimer Architectures: Total Syntheses of (−)-Lycodine and (−)-Complanadines A and B, and Evaluation of Their Neurite Outgrowth Activities | en |
dc.type | journal article | - |
dc.type.niitype | Journal Article | - |
dc.identifier.ncid | AA11076269 | - |
dc.identifier.jtitle | Chemistry - A European Journal | en |
dc.identifier.volume | 23 | - |
dc.identifier.issue | 4 | - |
dc.identifier.spage | 802 | - |
dc.identifier.epage | 812 | - |
dc.relation.doi | 10.1002/chem.201604647 | - |
dc.textversion | author | - |
dc.address | Department of Chemistry, Graduate School of Science, Tohoku University | en |
dc.address | Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Kyoto University | en |
dc.address | Department of Chemistry, Graduate School of Science, Tohoku University | en |
dc.address | Department of Molecular Pharmacology, Graduate School of Pharmaceutical Sciences, Kyoto University | en |
dc.address | Department of Molecular Pharmacology, Graduate School of Pharmaceutical Sciences, Kyoto University | en |
dc.address | Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Kyoto University | en |
dc.address | Department of Chemistry, Graduate School of Science, Tohoku University | en |
dc.identifier.pmid | 27758009 | - |
dcterms.accessRights | open access | - |
dc.identifier.pissn | 0947-6539 | - |
dc.identifier.eissn | 1521-3765 | - |
出現コレクション: | 学術雑誌掲載論文等 |
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