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Quinolizidines. VIII. Structure and Synthesis of the Alangium Alkaloid Alangicine : Syntheses of (±)- and (+)-Alangicines
http://hdl.handle.net/2297/7614
http://hdl.handle.net/2297/76142713f486-6f24-4484-9ea1-7ceafaf03418
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
PH-PR-OHBA-M-2583.pdf (1.3 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. VIII. Structure and Synthesis of the Alangium Alkaloid Alangicine : Syntheses of (±)- and (+)-Alangicines | |||||
| 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× Yamada, Koichiro× Minami, Shinzaburo× Yoshifuji, Shigeyuki× Ohba, Masashi |
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| 書誌情報 |
Chemical & pharmaceutical bulletin 巻 31, 号 8, p. 2583-2592, 発行日 1983-08-25 |
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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.31.2583 | |||||
| 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 | The first total synthesis of alangicine (3), an Alangium lamarckii alkaloid, has been achieved in the form of a racemic modification by means of an initial alkaline hydrolysis of the (±)-tricyclic ester 6 and succeeding steps proceeding through the intermediates (±)-7,(±)-10,and (±)-9. A parallel synthetic route starting with the (-)-tricyclic ester 6,derived from (+)-cincholoipon ethyl ester (8), produced the chiral target molecule (+)-3 with alangicine unequivocally established the structure and absolute stereochemistry of this alkaloid. The ^<13>C nuclear magnetic resonance spectra of (±)-alangicine (3) and the ipecac and Alangium alkaloid psychotrine (18) confirmed their endocyclic double bond structures in the dihydroisoquinoline moiety. Catalytic reductions of 11,(±)-12,and 15 using hydrogen and Pd-C were investigated, and the results have shown that hydrogenolysis of the benzyloxy group proceeds much faster than saturation of the endocyclic C=N bond. | |||||
| 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 | |||||
