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Quinolizidines. XXVIII. Racemic and chiral syntheses of ochromianine, an indoloquinolizidine alkaloid from Neisosperma miana
http://hdl.handle.net/2297/7592
http://hdl.handle.net/2297/759273139227-9b6f-41fc-93ac-c3be53d54bd8
名前 / ファイル | ライセンス | アクション |
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PE-PR-OHBA-M-75.pdf (815.1 kB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2017-10-03 | |||||
タイトル | ||||||
タイトル | Quinolizidines. XXVIII. Racemic and chiral syntheses of ochromianine, an indoloquinolizidine alkaloid from Neisosperma miana | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
著者 |
Fujii, Tozo
× Fujii, Tozo× Ohba, Masashi× Tachinami, Takeshi× Ohashi, Takako |
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書誌情報 |
Chemical & pharmaceutical bulletin 巻 39, 号 1, p. 75-78, 発行日 1991-01-25 |
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ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 0009-2363 | |||||
NCID | ||||||
収録物識別子タイプ | NCID | |||||
収録物識別子 | AA00602100 | |||||
DOI | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | DOI | |||||
関連識別子 | 10.1248/cpb.39.75 | |||||
出版者 | ||||||
出版者 | 日本薬学会 | |||||
抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | A full account is given of the first racemic and chiral syntheses of 11-methoxydihydrocorynantheol [(-)-1], a candidate structure for the Neisosperma alkaloid ochromianine. Coupling of (±)-trans-6-ethoxy-3-ethyl-2,3,4,5-tetrahydro-4-pyridineacetic acid ethyl ester [(±)-6] with 2-chloro-1-(6-methoxy-1H-indol-3-yl)ethanone (4) in the presence of KBr produced the lactam ketone (±)-7,which was then converted into the lactam (±)-9 through the oxazolium salt (±)-8. Bischler-Napieralski cyclization of (±)-9 followed by catalytic hydrogenation gave the tetracyclic ester (±)-11. On reduction with LiAlH_4,(±)-11 yielded the racemic target (±)-1. A parallel synthetic route starting from (+)-6 and 4 afforded the chiral target (-)-1 via (+)-7,8,(+)-9,and (-)-11. Identity of synthetic (-)-1 with ochromianine unequivocally established the structure and absolute stereochemistry of this alkaloid. | |||||
著者版フラグ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 |