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Volumn 8, Issue 17, 1997, Pages 2893-2903

Desymmetrization of bicyclo[3.3.0]octane-3,7-dione by the Schmidt reaction: An easy synthesis of tecomanine

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BICYCLO[3.3.0]OCTANE DERIVATIVE; TECOMINE; UNCLASSIFIED DRUG;

EID: 0030769704     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00308-X     Document Type: Article
Times cited : (19)

References (75)
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    • (d) Reissig, H.-U. The Weiss Reaction in Organic Synthesis Highlights, Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Editors; VHC: Weinheim, 1991, and references cited therein.
    • (1991) The Weiss Reaction in Organic Synthesis Highlights
    • Reissig, H.-U.1
  • 7
    • 0343006084 scopus 로고
    • Ph.D. Thesis, University of Wisconsin-Milwaukee, Milwaukee, WI
    • Lannoye, G. L. Ph.D. Thesis, University of Wisconsin-Milwaukee, Milwaukee, WI, 1987.
    • (1987)
    • Lannoye, G.L.1
  • 43
    • 77957083757 scopus 로고
    • Manske, R. H. F., Ed.; Academic Press: New York
    • (a) Cordell, G. A. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1977; vol. 16, p 431.
    • (1977) The Alkaloids , vol.16 , pp. 431
    • Cordell, G.A.1
  • 44
    • 77957051048 scopus 로고
    • Brossi, A., Ed.; Academic Press: Orlando
    • (b) Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1985; vol. 26, p 89.
    • (1985) The Alkaloids , vol.26 , pp. 89
    • Strunz, G.M.1    Findlay, J.A.2
  • 52
    • 0343376067 scopus 로고    scopus 로고
    • note
    • Three syntheses of tecomanine 4 have been published so far. (±)-4: ref 11 d-e; (+)-4: ref. 11f.
  • 57
    • 0028802610 scopus 로고
    • and pertinent references cited therein
    • (c) Evans, P. A.; Modi, D. P. J. Org. Chem. 1995, 60, 6662 and pertinent references cited therein.
    • (1995) J. Org. Chem. , vol.60 , pp. 6662
    • Evans, P.A.1    Modi, D.P.2
  • 64
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    • note
    • 3.
  • 66
    • 0343376054 scopus 로고    scopus 로고
    • note
    • In Schemes 1 and 2 all compounds are racemic; for convenience, only the enantiomer corresponding to natural tecomanine 4 is represented for each compound.
  • 70
    • 0342940718 scopus 로고    scopus 로고
    • note
    • 11d-f indicated that 4-methyl configuration in the tecomanine series can be controlled under basic or acidic equilibration conditions.
  • 71
    • 0343376053 scopus 로고    scopus 로고
    • note
    • A sample of natural tecomanine 4 was kindly supplied by Prof. G. Jones, University of Keele.
  • 73
    • 0343376052 scopus 로고    scopus 로고
    • note
    • 4-THF, 20°C.
  • 75
    • 0342940717 scopus 로고    scopus 로고
    • note
    • + force fields of Hyper-Chem (Release 3 for Windows), AUTODESK (1993).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.