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Volumn 8, Issue 18, 1997, Pages 3143-3151

Synthesis of enantiopure (2R,3aS,7aS)-2-ethyloctahydroindol-6-one and its Fischer indolization

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID; INDOLE DERIVATIVE;

EID: 0030884711     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00379-0     Document Type: Article
Times cited : (18)

References (29)
  • 2
    • 0017032571 scopus 로고
    • For leading references regarding isolation, characterization, biosynthesis and synthesis of ibophyllidine alkaloids, see: (a) Khuong-Huu, F.; Cesario, M.; Guilhem, J.; Goutarel, R. Tetrahedron 1976, 32, 2539.
    • (1976) Tetrahedron , vol.32 , pp. 2539
    • Khuong-Huu, F.1    Cesario, M.2    Guilhem, J.3    Goutarel, R.4
  • 6
    • 0005422544 scopus 로고
    • The ibogamine-catharanthine group
    • Monoterpenoid Indole Alkaloids, supplement to part 4, Saxton, J. E. ed., Taylor, E. C. ed., John Wiley, Chichester
    • (e) Saxton, J. E., "The Ibogamine-Catharanthine Group" in Monoterpenoid Indole Alkaloids, supplement to part 4, Saxton, J. E. ed., in The Chemistry of Heterocyclic Compounds, Taylor, E. C. ed., vol. 25, pp. 487-521, John Wiley, Chichester, 1994.
    • (1994) The Chemistry of Heterocyclic Compounds , vol.25 , pp. 487-521
    • Saxton, J.E.1
  • 11
    • 0000880590 scopus 로고
    • Siedel, W.; Sturm, K.; Geiger, R. Chem. Ber. 1963, 96, 1436-1440. Chem. Abstr. 1963, 59, 2951e.
    • (1963) Chem. Abstr. , vol.59
  • 16
    • 0342637873 scopus 로고    scopus 로고
    • note
    • The regioisomer 7 was formed as a by-product (approx. 10% yield). Reduction of the aziridinium intermediate depicted in the figure accounts for its formation. (matrix presented)
  • 24
    • 0014531898 scopus 로고
    • For interesting mechanistic aspects on the Fischer indolization upon β-amino ketones, see: Ban, Y.; Iijima, I. Tetrahedron Lett. 1969, 2523-2525; Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641-1653; Ball, J. B.; Bremmer, J. B.; Browne, E. J. Heterocycles 1987, 26, 1573-1580.
    • (1969) Tetrahedron Lett. , pp. 2523-2525
    • Ban, Y.1    Iijima, I.2
  • 25
    • 0017373420 scopus 로고
    • For interesting mechanistic aspects on the Fischer indolization upon β-amino ketones, see: Ban, Y.; Iijima, I. Tetrahedron Lett. 1969, 2523-2525; Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641-1653; Ball, J. B.; Bremmer, J. B.; Browne, E. J. Heterocycles 1987, 26, 1573-1580.
    • (1977) Tetrahedron , vol.33 , pp. 1641-1653
    • Lawton, G.1    Saxton, J.E.2    Smith, A.J.3
  • 26
    • 0342637871 scopus 로고
    • For interesting mechanistic aspects on the Fischer indolization upon β-amino ketones, see: Ban, Y.; Iijima, I. Tetrahedron Lett. 1969, 2523-2525; Lawton, G.; Saxton, J. E.; Smith, A. J. Tetrahedron 1977, 33, 1641-1653; Ball, J. B.; Bremmer, J. B.; Browne, E. J. Heterocycles 1987, 26, 1573-1580.
    • (1987) Heterocycles , vol.26 , pp. 1573-1580
    • Ball, J.B.1    Bremmer, J.B.2    Browne, E.J.3
  • 28
    • 0040483232 scopus 로고
    • For a discussion about the stereochemical factors influencing the regiochemical course of Fischer indole synthesis, see: Freter, K.; Fuchs, V.; Pitner, T. P. J. Org. Chem. 1983, 48, 4593-4597. See also, Hugues, D. L.; Zhao, D. J. Org. Chem. 1993, 58, 228-233.
    • (1983) J. Org. Chem. , vol.48 , pp. 4593-4597
    • Freter, K.1    Fuchs, V.2    Pitner, T.P.3
  • 29
    • 0000414271 scopus 로고
    • For a discussion about the stereochemical factors influencing the regiochemical course of Fischer indole synthesis, see: Freter, K.; Fuchs, V.; Pitner, T. P. J. Org. Chem. 1983, 48, 4593-4597. See also, Hugues, D. L.; Zhao, D. J. Org. Chem. 1993, 58, 228-233.
    • (1993) J. Org. Chem. , vol.58 , pp. 228-233
    • Hugues, D.L.1    Zhao, D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.