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Volumn , Issue 5, 2011, Pages 898-907

Conjugate addition of 2-acetylindole enolates to unsaturated oxazolopiperidone lactams: Enantioselective access to the tetracyclic ring system of ervitsine

Author keywords

Alkaloids; Asymmetric synthesis; Cyclization; Lactams; Michael addition; Nitrogen heterocycles

Indexed keywords


EID: 79551548128     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001020     Document Type: Article
Times cited : (7)

References (42)
  • 16
    • 33750459862 scopus 로고    scopus 로고
    • For conjugate addition reactions to polycyclic unsaturated lactams, see: E. García, E. Lete, N. Sotomayor, J. Org. Chem. 2006, 71, 6776-6784.
    • (2006) J. Org. Chem. , vol.71 , pp. 6776-6784
    • García, E.1    Lete, E.2    Sotomayor, N.3
  • 24
    • 79551507450 scopus 로고    scopus 로고
    • For the relative configuration at the epimerizable C-6 stereocenter, see the Exp. Section. The relative configuration at C-6 was deduced from the 6-H/7-H coupling constant of 6-H in the NMR spectra
    • For the relative configuration at the epimerizable C-6 stereocenter, see the Exp. Section. The relative configuration at C-6 was deduced from the 6-H/7-H coupling constant of 6-H in the NMR spectra.
  • 27
    • 79551533579 scopus 로고    scopus 로고
    • [3b,8,9]
    • [3b,8,9]
  • 28
    • 79551529676 scopus 로고    scopus 로고
    • note
    • +: 403.2016; found 403.2016.
  • 32
    • 0034625424 scopus 로고    scopus 로고
    • For recent reviews on the chemistry of N-acyliminium ions, see: W. N. Speckamp, M. J. Moolenaar, Tetrahedron 2000, 56, 3817-3856.
    • (2000) Tetrahedron , vol.56 , pp. 3817-3856
    • Speckamp, W.N.1    Moolenaar, M.J.2
  • 34
    • 0031009384 scopus 로고    scopus 로고
    • For the total synthesis of ervitsine in the racemic series, see: for the enantioselective synthesis of N-methylervitsine, see
    • M.-Ll. Bennasar, B. Vidal, J. Bosch, J. Org. Chem. 1997, 62, 3597-3609, for the enantioselective synthesis of N-methylervitsine, see
    • (1997) J. Org. Chem. , vol.62 , pp. 3597-3609
    • Bennasar, M.-Ll.1    Vidal, B.2    Bosch, J.3
  • 37
    • 79551522084 scopus 로고    scopus 로고
    • note
    • +: 403.2016; found 403.2014.
  • 39
    • 0019775986 scopus 로고
    • For the chemoselective oxidation of a 2-indolylmethyl to a 2-acylindole moiety, see: Y. Ban, K. Yoshida, J. Goto, T. Oishi, J. Am. Chem. Soc. 1981, 103, 6990-6992.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 6990-6992
    • Ban, Y.1    Yoshida, K.2    Goto, J.3    Oishi, T.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.