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Volumn 8, Issue 6, 2006, Pages 1037-1040

Ancisheynine, the first N,C-coupled naphthylisoquinoline alkaloid: Total synthesis and stereochemical analysis

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANCISHEYNINE; ISOQUINOLINE DERIVATIVE; NAPHTHALENE DERIVATIVE;

EID: 33646448276     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052946p     Document Type: Article
Times cited : (65)

References (38)
  • 1
    • 77957089074 scopus 로고
    • Cordell, G. A., Ed.; Academic Press: San Diego
    • Bringmann, G.; Pokorny, F. The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1995; Vol. 46, p 127.
    • (1995) The Alkaloids , vol.46 , pp. 127
    • Bringmann, G.1    Pokorny, F.2
  • 14
    • 33646454318 scopus 로고    scopus 로고
    • note
    • For the biosynthetic formation of 3 (as also of 1 and 2), a separate formation of the isoquinoline and naphthalene portions is assumed, followed by an oxidative phenolic cross-coupling.
  • 23
    • 33646438281 scopus 로고    scopus 로고
    • note
    • f value as compared to 1-aminonaphthalene), turning violet during exposure to air, which hints at the presence of an electron-rich aminonaphthalene.
  • 25
    • 0001628090 scopus 로고    scopus 로고
    • The only information known about the required properties of counteranions of isoquinolinium salts is that they should not be nucleophilic. In this respect, even chloride was reactive enough to compete with the N-nucleophile, thus causing decomposition of the isoquinolinium salt, e.g., in Zincke reactions. For details, see: Barbier, D.; Marazano, C.; Das, B. C.; Potier, P. J. Org. Chem. 1996, 61, 9596.
    • (1996) J. Org. Chem. , vol.61 , pp. 9596
    • Barbier, D.1    Marazano, C.2    Das, B.C.3    Potier, P.4
  • 28
    • 33646439590 scopus 로고    scopus 로고
    • note
    • Analysis of the er of the isolated enantiomers of 3c over a period of 600 min showed no atropisomerization.
  • 32
    • 33646448169 scopus 로고    scopus 로고
    • note
    • The CD spectra of those structures that lie energetically higher than 3 kcal/mol above the global minimum do not significantly contribute to the overall CD curve.
  • 34
    • 0000750794 scopus 로고    scopus 로고
    • Schreier, P., Herderich, M., Humpf, H. U., Schwab, W., Eds.; Vieweg: Wiesbaden
    • Bringmann, G.; Busemann, S. Natural Product Analysis; Schreier, P., Herderich, M., Humpf, H. U., Schwab, W., Eds.; Vieweg: Wiesbaden, 1998; p 195.
    • (1998) Natural Product Analysis , pp. 195
    • Bringmann, G.1    Busemann, S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.