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Volumn 5, Issue 6, 2003, Pages 921-923

Preparation of the 4-hydroxytryptamine scaffold via palladium-catalyzed cyclization: A practical and versatile synthesis of psilocin

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYTRYPATAMINE; ACETYLENE DERIVATIVE; ANILINE DERIVATIVE; CARBONYL DERIVATIVE; N TERT BUTOXYCARBONYL 2 IODO 3 METHOXYANILINE; PALLADIUM; PSILOCIN; TRYPTAMINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0038223924     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0341039     Document Type: Article
Times cited : (56)

References (31)
  • 2
    • 0001677680 scopus 로고
    • ApSimon, J., Ed.; Wiley-Interscience: New York
    • (b) Kutney, J. P. Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley-Interscience: New York, 1977; Vol. 3, p 273.
    • (1977) Total Synthesis of Natural Products , vol.3 , pp. 273
    • Kutney, J.P.1
  • 18
    • 0141597521 scopus 로고    scopus 로고
    • (Nippon Zeon Co., Ltd., Japan) Jpn. Kokai Tokkyo Koho JP 2000044555, 2000
    • Aldrich: 4-benzyloxyindole (1 g), $A225; 4-hydroxyindole (1 g), $A288 (1/2003). A patent describing an efficient synthesis of 4-hydroxyindoles from cyclohexane-1,3-dione, where the key step is the reaction of oxochromancarboxylic acid derivatives with ammonia in methanol in an autoclave, has been filed. The author notes that this may effect the price of 4-hydroxyindoles in the future. Matsuura, T. (Nippon Zeon Co., Ltd., Japan) Jpn. Kokai Tokkyo Koho JP 2000044555, 2000.
    • Matsuura, T.1
  • 24
    • 0141485863 scopus 로고    scopus 로고
    • UK Pat. Appl. GB2328941, 1999
    • Smith, A. L. Brit. UK Pat. Appl. GB2328941, 1999.
    • Smith, A.L.1
  • 27
    • 0141709207 scopus 로고    scopus 로고
    • note
    • Preparation of 14 g of 3 was performed in our laboratories using standard glassware.
  • 28
    • 0141820521 scopus 로고    scopus 로고
    • note
    • This substitution reaction was accomplished successfully using an aqueous solution of N,N-dimethylamine with no formation of 3-butyn-1-ol detected by NMR. Previous methods have used N,N-dimethylamine as a gas or dissolved in an organic solvent; both of these sources of N,N-dimethylamine are considerably more expensive or inconvenient to use.
  • 29
    • 0141597518 scopus 로고    scopus 로고
    • note
    • 4OH) to give the title compound as a light brown oil in 69% yield (2.45 g, 6.3 mmol).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.