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Volumn 53, Issue 48, 1997, Pages 16565-16574

A short, enantioselective synthesis of (-)-epilupinine from proline via a spirocyclic ammonium ylide

Author keywords

[No Author keywords available]

Indexed keywords

LUPININE; MATRINE;

EID: 0030830828     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)01037-5     Document Type: Conference Paper
Times cited : (63)

References (48)
  • 1
    • 0002417028 scopus 로고
    • Cordell, G. A., Ed.; Academic Press: San Diego, CA, Ch. 1
    • Reviews: (a) Ohmiya, S.; Saito, K.; Murakoshi, I. In The Alkaloids, Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1995; Vol. 47, Ch. 1.
    • (1995) The Alkaloids , vol.47
    • Ohmiya, S.1    Saito, K.2    Murakoshi, I.3
  • 3
  • 8
    • 0342495767 scopus 로고
    • (d) Li, X.; Dai, S.; Li, W.; Zhou, Y.; Zhao, X.; Gao, L. Zhongcaoyao 1987, 18, 214; Chem. Abst. 1987, 107, 126695.
    • (1987) Chem. Abst. , vol.107 , pp. 126695
  • 14
    • 0027370868 scopus 로고
    • (e) Cordero, F. M.; Anichini, B.; Goti, A.; Brandi, A. Tetrahedron 1993, 49, 9867. For a more extensive list of synthetic routes to lupinine and epilupinine, see ref. 5, footnote 4.
    • (1993) Tetrahedron , vol.49 , pp. 9867
    • Cordero, F.M.1    Anichini, B.2    Goti, A.3    Brandi, A.4
  • 31
    • 0342495759 scopus 로고    scopus 로고
    • note
    • 6'7
  • 32
    • 0343365218 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, Ch. 3.10
    • Reviews of the Stevens and related rearrangements: (a) Markó, I. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, Ch. 3.10.
    • (1991) Comprehensive Organic Synthesis , vol.3
    • Markó, I.E.1
  • 35
    • 0342929930 scopus 로고    scopus 로고
    • note
    • A smaller excess of proline ester could be used with little or no diminution of yield in larger scale reactions (≥20 mmol of the bromide).
  • 40
    • 0343365213 scopus 로고    scopus 로고
    • note
    • Naturally occurring epilupinine exists as the (+)-enantiomer. It is presumed that this antipode would be available via an analogous route starting with D-proline benzyl ester.
  • 47
    • 0041966858 scopus 로고
    • Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York
    • (b) Porter, N. A.; Krebs, P. J. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1988; Vol. 18.
    • (1988) Topics in Stereochemistry , vol.18
    • Porter, N.A.1    Krebs, P.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.