Quinolizidines. XV. A Racemic Synthesis of 10-Demethyltubulosine, an Alkaloid from Alangium lamarckii
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概要
- 論文の詳細を見る
The racemic synthesis of the Alangium lamarckii alkaloid 10-demethyltubulosine (2) has been accomplished for the first time via a "lactim ether route, "which included the intermediates (±)-7,(±)-8,(±)-10,and (±)-9. The 1'α-H isomers (±)-12 and (±)-11 were also obtained through this synthetic route. The assignments of the configuration at C-1'of (±)-2,(±)-9,(±)-11,and (±)-12 were based on four criteria, namely, the ratio of products from the catalytic reduction of (±)-10,thin-layer chromatographic mobility, and ^1H and ^<13>C nuclear magnetic resonance spectral features. The identity of synthetic (±)-2 with (-)-demethyltubulosine from A. lamarckii unequivocally established the structure of this alkaloid.
- 公益社団法人日本薬学会の論文
- 1985-10-25
著者
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藤井 澄三
Faculty Of Pharmaceutical Sciences Kanazawa University
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大場 正志
Faculty of Pharmaceutical Sciences, Kanazawa University
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大場 正志
Kanazawa Univ. Ishikawa Jpn
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Ohba M
Faculty Of Pharmaceutical Sciences Kanazawa University
関連論文
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- Purines. LI. Synthesis and Biological Activity of Hypoxanthine 7-N-Oxide and Related Compounds
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- Lactams. VII. Stereochemical Characterization and Cis-Trans Isomerization of 5-Ethyl-2-oxo-4-piperidineacetic Acid and Related Compounds
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- Quinolizidines. XXVI. : A Synthesis of (±)-Deplancheine
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- Purines. XLIII. : A Total Synthesis of the Marine Sponge Base 6-Imino-1,9-dimethyl-8-oxopurine
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- Lactams. XI. Construction of Lactam Carbonyl Function in 1,3-Disubstituted Piperidines by Mercuric Acetate-EDTA Oxidation : Effects of Carbonyl and Related Groups at the 3-Position
- Lactams. IX. Generation of Lactam Carbonyl Function in 1,3-Disubstituted Piperidines by Mercuric Acetate-EDTA Oxidation : Effects of Hydrocarbon Substituents at the 3-Position