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Volumn 105, Issue 16, 1983, Pages 5373-5379

Importance of Allylic Interactions and Stereoelectronic Effects in Dictating the Steric Course of the Reaction of Iminium Ions with Nucleophiles. An Efficient Total Synthesis of (±)-Gephyrotoxin

Author keywords

[No Author keywords available]

Indexed keywords

GEPHYROTOXIN;

EID: 0021091145     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00354a031     Document Type: Article
Times cited : (116)

References (52)
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    • For a recent review of these fascinating natural products, See
    • For a recent review of these fascinating natural products, See: Daly, J.W. Fortschr. Chem. Org. Naturst. 1982, 41, 205-340.
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  • 6
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    • For a total synthesis of (+)-gephyrotoxin, See:, There is current disagreement on the absolute configuration of the natural alkaloid.
    • For a total synthesis of (+)-gephyrotoxin, See: Fujimoto, R.; Kishi, Y. Tetrahedron Lett. 1981, 42, 4197-4198. There is current disagreement on the absolute configuration of the natural alkaloid.
    • (1981) Tetrahedron Lett. , vol.42 , pp. 4197-4198
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    • For previous total synthesis of (±)-gephyrotoxin, see
    • For previous total synthesis of (±)-gephyrotoxin, see: Fujimoto, R.; Kishi, Y.J. Am. Chem. Soc. 1980, 102, 7154-7156.
    • (1980) Am. Chem. Soc. , vol.102 , pp. 7154-7156
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  • 9
    • 0006751710 scopus 로고
    • For a formal total synthesis, See
    • For a formal total synthesis, See: Hart, D.J. J. Org. Chem. 1981, 46, 3576-3578.
    • (1981) J. Org. Chem. , vol.46 , pp. 3576-3578
    • Hart, D.J.1
  • 10
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    • For previous total syntheses of (±)-perhydrogephyrotoxin, See
    • For previous total syntheses of (±)-perhydrogephyrotoxin, See: (a) Overman, L.E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454-1456.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 1454-1456
    • Overman, L.E.1    Fukaya, C.2
  • 12
    • 0042711408 scopus 로고
    • For syntheses of the racemic perhydropyrrolo[1, 2-a]quinoline ring system, See
    • For syntheses of the racemic perhydropyrrolo[1, 2-a]quinoline ring system, See: Habermehl, G.G.; Thurau, O. Naturwissenschaften 1980, 67, 193.
    • (1980) Naturwissenschaften , vol.67 , pp. 193
    • Habermehl, G.G.1    Thurau, O.2
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    • For a review, See
    • For a review, See: Johnson, F. Chem. Rev. 1968, 68, 375-413.
    • (1968) Chem. Rev. , vol.68 , pp. 375-413
    • Johnson, F.1
  • 23
    • 85022924645 scopus 로고    scopus 로고
    • ref 3 and structure 1
    • The numbering used for all intermediates corresponds to that of gephyrotoxin; see
    • The numbering used for all intermediates corresponds to that of gephyrotoxin; see ref 3 and structure 1.
  • 25
    • 85022964223 scopus 로고    scopus 로고
    • ref 8a
    • A modification of this strategy, which culminated in the first synthesis of perhydrogephyrotoxin, is described in
    • A modification of this strategy, which culminated in the first synthesis of perhydrogephyrotoxin, is described in ref 8a.
  • 26
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    • For related conversions of lactams to iminium ions (or the related enamines), See
    • For related conversions of lactams to iminium ions (or the related enamines), See: Bohlmann, F.; Müller, H.-J.; Schumann, D. Chem. Ber. 1973, 106, 3026-3034.
    • (1973) Chem. Ber. , vol.106 , pp. 3026-3034
    • Bohlmann, F.1    Müller, H.-J.2    Schumann, D.3
  • 29
    • 85022909874 scopus 로고    scopus 로고
    • Unpublished studies of Dr. Peter Jessup. The approach was identical with that described in ref 16
    • Unpublished studies of Dr. Peter Jessup. The approach was identical with that described in ref 16.
  • 32
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    • The Chemistry of Organolithium Compounds
    • Cf.:, Pergamon: Oxford, Chapter 1.
    • Cf.: Wakefield, B.J. “The Chemistry of Organolithium Compounds”; Pergamon: Oxford, 1974; Chapter 1.
    • (1974)
    • Wakefield, B.J.1
  • 34
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    • A 20-cm DuPont Zorbax PSM-60 column and a 1:4 ethyl acetate/ hexane eluent were used for this analysis
    • A 20-cm DuPont Zorbax PSM-60 column and a 1:4 ethyl acetate/ hexane eluent were used for this analysis.
  • 36
    • 85022962986 scopus 로고    scopus 로고
    • These experiments were conducted by R. Freerks
    • These experiments were conducted by R. Freerks.
  • 41
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    • (a) Deprotection under reductive conditions8b, 33b was markedly inferior. (b) Cf.
    • (a) Deprotection under reductive conditions8b, 33b was markedly inferior. (b) Cf.: Just, G.; Grozinger, K. Synthesis 1976, 457-458.
    • (1976) Synthesis , pp. 457-458
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  • 49
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    • A 25-m SE-30 glass capillary column was used for this analysis
    • A 25-m SE-30 glass capillary column was used for this analysis.
  • 52
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    • Multiple! resolved by resolution enhancement
    • Multiple! resolved by resolution enhancement.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.