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Volumn 4, Issue 19, 2002, Pages 3329-3332

6-Exo-spiro (alkoxycarbonylamino)methyl radical cyclization: Highly regio- and stereoselective synthesis of (-)-sibirine

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; SIBIRINE; SPIRO COMPOUND;

EID: 0037136499     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026671e     Document Type: Article
Times cited : (29)

References (68)
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    • Martin, S.F.1
  • 2
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    • (b) Fuji, K. Chem. Rev. 1993, 93, 2037-2066. For reviews on the synthesis of spiro systems, see:
    • (1993) Chem. Rev. , vol.93 , pp. 2037-2066
    • Fuji, K.1
  • 12
    • 0042317813 scopus 로고    scopus 로고
    • 9062-9066 in ref 1d
    • (h) pp 9062-9066 in ref 1d.
  • 26
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    • For the use of the PhSe group for the generation of a radical α to a lactam nitrogen, see: (a) Bachi, M. D.; Hoornaert, C. Tetrahedron Lett. 1981, 2693-2694.
    • (1981) Tetrahedron Lett. , pp. 2693-2694
    • Bachi, M.D.1    Hoornaert, C.2
  • 32
    • 0001213699 scopus 로고
    • For the synthesis of sibirine and other Nitraria alkaloids, see: (a) Snider, B. B.; Cartaya-Marin, C. J. Org. Chem. 1984, 49, 1688-1691.
    • (1984) J. Org. Chem. , vol.49 , pp. 1688-1691
    • Snider, B.B.1    Cartaya-Marin, C.2
  • 59
    • 0001786881 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weinheim, Germany
    • (d) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 1998; pp 44-97.
    • (1998) Metal-catalyzed Cross-Coupling Reactions , pp. 44-97
    • Suzuki, A.1
  • 60
    • 0041316393 scopus 로고    scopus 로고
    • note
    • 4 and the resulting, still inseparable mixture of the N-methyl compounds was analyzed.
  • 61
    • 0000848607 scopus 로고
    • For the use of the phenylsulfonyl group as a radical acceptor, see, e.g.: (a) Clive, D. L. J.; Bergstra, R. J. J. Org. Chem. 1990, 55, 1786-1792.
    • (1990) J. Org. Chem. , vol.55 , pp. 1786-1792
    • Clive, D.L.J.1    Bergstra, R.J.2
  • 64
    • 0042818976 scopus 로고    scopus 로고
    • For some unknown reason, the two-step sequence toward 19 via the tri(n-butyl)stannylmethyl derivative of 18 proved to be much less efficient
    • For some unknown reason, the two-step sequence toward 19 via the tri(n-butyl)stannylmethyl derivative of 18 proved to be much less efficient.
  • 65
    • 0041316394 scopus 로고    scopus 로고
    • In addition, the dealkylaled product 18 was also isolated (<10%)
    • In addition, the dealkylaled product 18 was also isolated (<10%).
  • 68
    • 0000465995 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Germany
    • (b) Itsuno, S. In Comprehensive Asymmetric Catalysis: Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Germany, 1999; Vol. I, pp 289-315.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 289-315
    • Itsuno, S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.