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Volumn 124, Issue 49, 2002, Pages 14546-14547

Enantioselective total synthesis of (-)-strychnine using the catalytic asymmetric Michael reaction and tandem cyclization

Author keywords

[No Author keywords available]

Indexed keywords

STRYCHNINE;

EID: 0037065336     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028457r     Document Type: Article
Times cited : (129)

References (34)
  • 1
    • 0034273688 scopus 로고    scopus 로고
    • For a representative review, see: Bonjoch, J.; Solé, D. Chem. Rev. 2000, 100, 3455.
    • (2000) Chem. Rev. , vol.100 , pp. 3455
    • Bonjoch, J.1    Solé, D.2
  • 5
    • 0013848559 scopus 로고
    • The numbering system and ring labeling based on the biogenetic interrelationship of indole alkaloids is used throughout this paper: Le Men, J.; Taylor, W. I. Experientia 1965, 21, 508.
    • (1965) Experientia , vol.21 , pp. 508
    • Le Men, J.1    Taylor, W.I.2
  • 13
    • 0027729380 scopus 로고
    • (e) Kuehne, M. E.; Xu, F. J. Org. Chem. 1993, 58, 7490. Kuehne, M. E.; Xu, F. J. Org. Chem. 1998, 63, 9427.
    • (1993) J. Org. Chem. , vol.58 , pp. 7490
    • Kuehne, M.E.1    Xu, F.2
  • 14
    • 0032509490 scopus 로고    scopus 로고
    • (e) Kuehne, M. E.; Xu, F. J. Org. Chem. 1993, 58, 7490. Kuehne, M. E.; Xu, F. J. Org. Chem. 1998, 63, 9427.
    • (1998) J. Org. Chem. , vol.63 , pp. 9427
    • Kuehne, M.E.1    Xu, F.2
  • 23
    • 0011987876 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 27
    • 0011918073 scopus 로고    scopus 로고
    • note
    • Both diastereomers were expected to be applicable to the synthesis because the C16 stereocenter can be epimerized during the last stage. Unexpected aromatization, however, proceeded in the next iodination step when 14β was used.
  • 28
    • 0011947583 scopus 로고    scopus 로고
    • note
    • (2-Nitrophenyl)ketone moiety was selected as a latent form of the indoline based on the previous results, see ref 4g.
  • 30
    • 0000366419 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford; Chapter 4.3
    • For a general review, see: Caubère, P.; Coutrot, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Chapter 4.3, Vol. 8, p 835.
    • (1991) Comprehensive Organic Synthesis , vol.8 , pp. 835
    • Caubère, P.1    Coutrot, P.2
  • 31
    • 4243746641 scopus 로고
    • and references therein
    • The transformation of strychnine to neostrychnine by normal Raney Ni in EtOH was reported, see: Beddoes, R. L.; Gorman, A. A.; Prescott, A. L. Acta Crystallogr. 1994, C50, 447 and references therein.
    • (1994) Acta Crystallogr , vol.C50 , pp. 447
    • Beddoes, R.L.1    Gorman, A.A.2    Prescott, A.L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.