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Volumn , Issue 3, 1998, Pages 435-440

Stereoselective total synthesis of enantiomerically pure 1-trifluoromethyl tetrahydroisoquinoline alkaloids

Author keywords

Alkaloids; Fluorine; Pictet spengler reaction; Quaternary stereocentre; Iminosulfoxides

Indexed keywords


EID: 0002154430     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199803)1998:3<435::AID-EJOC435>3.0.CO;2-2     Document Type: Article
Times cited : (42)

References (60)
  • 1
    • 0001521888 scopus 로고
    • [1a] K. Fuji, Chem. Rev. 1993, 93, 2037-2066.
    • (1993) Chem. Rev. , vol.93 , pp. 2037-2066
    • Fuji, K.1
  • 9
    • 2742581453 scopus 로고    scopus 로고
    • [2f] Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; G. Resnati, V. A. Soloshonok, Eds.; Tetrahedron Symposium-in-Print N 58; Tetrahedron 1996, 52, 1-330.
    • Tetrahedron Symposium-in-Print N 58
  • 10
    • 0001834676 scopus 로고    scopus 로고
    • [2f] Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; G. Resnati, V. A. Soloshonok, Eds.; Tetrahedron Symposium-in-Print N 58; Tetrahedron 1996, 52, 1-330.
    • (1996) Tetrahedron , vol.52 , pp. 1-330
  • 13
    • 2742511137 scopus 로고
    • A. S. Golubev, N. D. Chkanikov, M. Yu. Antipin, Yu. T. Struchkov, A. F. Kolomiets, A. V. Fokin, Izv. Akad. Nauk, Ser. Khim. 1992, 1831-1836 (Chem. Abs., 1993, 118, 101 844).
    • (1993) Chem. Abs. , vol.118 , pp. 101844
  • 21
    • 0001251131 scopus 로고
    • [4h] For some reviews on tetrahydroisoquinoline alkaloids: M. D. Rozwadowska, Heterocycles 1994, 39, 903-931.
    • (1994) Heterocycles , vol.39 , pp. 903-931
    • Rozwadowska, M.D.1
  • 27
    • 37049067217 scopus 로고
    • [6a] For the stereoselective syntheses of fluorine-free tetrahydroisoquinoline and β-carboline alkaloids via chiral sulfoxide chemistry: S. G. Pyne, S. L. Chapman, J Chem Soc., Chem Commun 1986, 1688-1689.
    • (1986) J Chem Soc., Chem Commun , pp. 1688-1689
    • Pyne, S.G.1    Chapman, S.L.2
  • 37
    • 0030960045 scopus 로고    scopus 로고
    • Corrigenda: Tetrahedron Lett. 1997, 38, 6477
    • S. Fustero, A. Navarro, A. Asensio, Tetrahedron Lett. 1997, 38, 4891-4894. Corrigenda: Tetrahedron Lett. 1997, 38, 6477.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 4891-4894
    • Fustero, S.1    Navarro, A.2    Asensio, A.3
  • 39
    • 4243241249 scopus 로고
    • [10b] For a review on the Pictet-Spengler reaction: A. D. Cox, J. M. Cook, Chem. Rev. 1995, 95, 1797-1842.
    • (1995) Chem. Rev. , vol.95 , pp. 1797-1842
    • Cox, A.D.1    Cook, J.M.2
  • 43
    • 2742512202 scopus 로고    scopus 로고
    • note
    • [6f]
  • 46
    • 2742530976 scopus 로고    scopus 로고
    • See also ref. 6g
    • [13c]See also ref. 6g.
  • 47
    • 84987548215 scopus 로고
    • The tetrahydroisoquinoline alkaloid carnegine can be extracted from Carnegiea gigantea. For its synthesis see: E. Spath, F. Dengel, Ber. Dtsch. Chem. Ges. 1938, 71B, 113-119.
    • (1938) Ber. Dtsch. Chem. Ges. , vol.71 B , pp. 113-119
    • Spath, E.1    Dengel, F.2
  • 49
  • 50
    • 0007235441 scopus 로고
    • Paquette, L. A. Ed.; John Wiley and Sons: New York
    • [15c] O. De Lucchi, U. Miotti, G. Modena, in Organic Reactions; Paquette, L. A. Ed.; John Wiley and Sons: New York, 1991, Vol. 40.
    • (1991) Organic Reactions , vol.40
    • De Lucchi, O.1    Miotti, U.2    Modena, G.3
  • 52
    • 2742584828 scopus 로고
    • [16a] The tetrahydroisoquinoline alkaloid calycotomine can be extracted from the seeds of Cytisus proliferus. For its synthesis see: A. Chatterjee, N. Adityachaudhury, J. Org. Chem. 1962, 27, 309-310.
    • (1962) J. Org. Chem. , vol.27 , pp. 309-310
    • Chatterjee, A.1    Adityachaudhury, N.2
  • 53
    • 2742611383 scopus 로고    scopus 로고
    • note
    • 4 in acetone/water (5:1) at room temperature we obtained complex mixtures of unidentified by-products.
  • 56
    • 0346322442 scopus 로고
    • S.-M. Nasirov, I. A. Israilov, L. G. Kuz'mina, M. S. Yunusov, Yu. T. Struchkov, S. Yu. Yunusov, Khim. Prir. Soedin. 1978, 752-758 (Chem. Abs., 1979, 91, 20 829).
    • (1979) Chem. Abs. , vol.91 , pp. 20829
  • 57
    • 2742562777 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100794. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44(1223) 336-033, e-mail: teched@chemcrys.cam.ac.uk].
  • 58
    • 0004150157 scopus 로고    scopus 로고
    • Siemens Analitical, X-ray Instruments, Inc., Madison, Wiscosin, U.S.A.
    • G.M Sheldrick, SHELXTL-plus, Siemens Analitical, X-ray Instruments, Inc., Madison, Wiscosin, U.S.A., 1989.
    • (1989) SHELXTL-plus
    • Sheldrick, G.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.