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Quinolizidines. XVIII. Synthesis of (-)- and (+)-ankorines through a lactim ether route
http://hdl.handle.net/2297/7605
http://hdl.handle.net/2297/7605d384d578-b260-4792-a498-329586de7a3a
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
PH-PR-OHBA-M-669.pdf (1.7 MB)
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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. XVIII. Synthesis of (-)- and (+)-ankorines through a lactim ether route | |||||
| 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× Yoneyama, Kaoru× Kizu, Hiroko× Yoshifuji, Shigeyuki |
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| 書誌情報 |
Chemical & pharmaceutical bulletin 巻 34, 号 2, p. 669-676, 発行日 1986-02-25 |
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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.34.669 | |||||
| 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 formal chiral synthesis of the Alangium alkaloid (-)-ankorine [(-)-6] has been accomplished in the form of the synthesis of the lactam phenol (+)-14 from the (+)-trans-lactim ether (+)-5 and 2-benzyloxy-3,4-dimethoxyphenacyl bromide through the intermediates (+)-10 and 11. A parallel sequence of conversions starting from the (-)-trans-lactim ether (-)-5 and proceeding through the intermediates (-)-10,24,(-)-14,(-)-15,26,(+)-27,and (+)-28 produced the enantiomer [(+)-6] of natural ankorine. For an alternative chial synthesis of (-)-6,ethyl cincholoiponate [(+)-19] was acetylated and the resulting N-acetyl derivative (+)-20-was oxidized with RuO_4 to give the 6-piperidone (+)-21,and 2-piperidone (-)-23 in 55% and 27% yields, respectively. The (-)-cis-lactim ether (-)-16,obtained by ethylation of (+)-21 with triethyl-oxonium fluoroborate, was then converted into (-)-13,a known precursor for the synthesis of (-)-ankorine [(-)-6], in good overall yield by a "lactim ether route, " which proceeded through (+)-15 and 12. | |||||
| 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 | |||||
