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Quinolizidines. X. Stereospecific Syntheses of (±)-9-Demethylpsychotrine and (±)-10-Demethylpsychotrine
http://hdl.handle.net/2297/7611
http://hdl.handle.net/2297/76118646e6d4-f97c-4d56-90a0-5e76950f5f40
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
PH-PR-OHBA-M-144-2.pdf (1.1 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. X. Stereospecific Syntheses of (±)-9-Demethylpsychotrine and (±)-10-Demethylpsychotrine | |||||
| 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 |
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| 書誌情報 |
Chemical & pharmaceutical bulletin 巻 33, 号 1, p. 144-151, 発行日 1985-01-25 |
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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.33.144 | |||||
| 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 | With the aim of establishing the structure of the Alangium alkaloid desmethylpsychotrine, stereospecific syntheses of two alternative structures, (±)-9-demethylpsychotrine (1) and (±)-10-demethylpsychotrine (2), have been achieved through a"lactim ether route."The synthesis of (±)-1 started with an initial condensation of the lactim ether 6,derived from the translactam ester 5,with 3-benzyloxy-4-methoxyphenacyl bromide (7a) and proceeded through the intermediates 8a, 9a, 10c, 10a, 11a, 12a, 13a, 14a, and 15a. A parallel sequence of conversions starting with 6 and 4-benzyloxy-3-methoxyphenacyl bromide (7b) produced (±)-2. The ^<13>C nuclear magnetic resonance spectra of (±)-1 and (±)-2 confirmed their endocyclic double bond structure in the dihydroisoquinoline moiety. Spectral comparison of (±)-1 and (±)-2 with natural desmethylpsychotrine suggested formula 1 to be the most likely structure 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 | |||||
