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Volumn 63, Issue 25, 1998, Pages 9146-9147

A general, stereocontrolled route to the geissoschizine family of alkaloids. Concise synthesis of the apogeissoschizine skeleton

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CARBOLINE DERIVATIVE; GEISSOSCHIZINE;

EID: 0032509487     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981415u     Document Type: Article
Times cited : (43)

References (31)
  • 6
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    • An approach to akagerine via the apogeissoschizine skeleton has been realized: Benson, W.; Winterfeldt, E. Heterocycles 1981, 15, 935
    • (1981) Heterocycles , vol.15 , pp. 935
    • Benson, W.1    Winterfeldt, E.2
  • 10
    • 0032580376 scopus 로고    scopus 로고
    • For recent reviews of this area, see: (c) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (e) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037.
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 11
    • 28244440935 scopus 로고    scopus 로고
    • For recent reviews of this area, see: (c) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (e) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037.
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 371
    • Armstrong, S.K.1
  • 12
    • 0032580376 scopus 로고    scopus 로고
    • For recent reviews of this area, see: (c) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (e) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2037.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2037
    • Schuster, M.1    Blechert, S.2
  • 22
    • 20644453913 scopus 로고    scopus 로고
    • note
    • 2) underwent dealkylation when subjected to Jeffrey's conditions.
  • 23
    • 20644457872 scopus 로고    scopus 로고
    • note
    • In the absence of potassium carbonate, the reaction stopped after reaching ca. 20% conversion with 10 mol % catalyst loading (or 55% with 30 mol % catalyst loading), presumably because the bromide anion inhibited the reaction. Addition of silver phosphate or carbonate also resulted in high conversions, but the reaction mixtures were not clean.
  • 25
    • 0023747588 scopus 로고
    • Yamaguchi, R.; Otsuji, A.; Utimoto, K.; Kozima, S. Bull. Chem. Soc. Jpn. 1992, 65, 298. See also: Martin, S. F.; Benage, B.; Hunter, J. E. J. Am. Chem. Soc. 1988, 110, 5925.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5925
    • Martin, S.F.1    Benage, B.2    Hunter, J.E.3
  • 27
    • 20644452821 scopus 로고    scopus 로고
    • note
    • 17,20 (Chemical Equation Presented)
  • 29
    • 20644468976 scopus 로고    scopus 로고
    • note
    • 2S as a HOCl scavenger has not previously been reported and represents a useful modification of the standard sodium chlorite oxidation of aldehydes to carboxylic acids.
  • 30
    • 0042186244 scopus 로고
    • Paquette, L. A., Ed.; Wiley: New York
    • For a comparative listing of HOCl scavengers employed in chlorite oxidation, see: Hase, T.; Wähälä, K. in Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 7, p 4533.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.7 , pp. 4533
    • Hase, T.1    Wähälä, K.2
  • 31
    • 20644452819 scopus 로고    scopus 로고
    • note
    • We thank Professor Stephen F. Martin (University of Texas, Austin) for generously providing an authentic sample of 15 for direct comparison.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.