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Volumn 61, Issue 16, 1996, Pages 5581-5586

Oxidative deamination of tetrahydroanabasine with o-quinones: An easy entry to lupinine, sparteine, and anabasine

Author keywords

[No Author keywords available]

Indexed keywords

ANABASINE; LUPININE; SPARTEINE;

EID: 0029784332     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9602130     Document Type: Article
Times cited : (45)

References (31)
  • 1
    • 77957062955 scopus 로고
    • Chemistry, Biochemistry and Chemotaxonomy of Lupine Alkaloids in the Leguminosae
    • Atta-ur-Rahman, Ed.; Elsevier: Amsterdam
    • For a recent review see: Saito, K.; Murakoshi, I. Chemistry, Biochemistry and Chemotaxonomy of Lupine Alkaloids in the Leguminosae. In Studies in Natural Products Chemistry 15; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1995; p 519.
    • (1995) Studies in Natural Products Chemistry 15 , pp. 519
    • Saito, K.1    Murakoshi, I.2
  • 9
    • 0000763694 scopus 로고
    • Corey E. J.; Achiwa, K. J. Am. Chem. Soc. 1969, 91, 1429. For further studies with quinone 13, see: Klein, R. F. X.; Bargas, L. M.; Horak, V. J. Org. Chem. 1988, 53, 5994. Vander Zwan, M. C.; Hartner, F. W.; Reamer, R. A.; Tull, R. J. Org. Chem. 1978, 43, 509.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 1429
    • Corey, E.J.1    Achiwa, K.2
  • 10
    • 0001164447 scopus 로고
    • Corey E. J.; Achiwa, K. J. Am. Chem. Soc. 1969, 91, 1429. For further studies with quinone 13, see: Klein, R. F. X.; Bargas, L. M.; Horak, V. J. Org. Chem. 1988, 53, 5994. Vander Zwan, M. C.; Hartner, F. W.; Reamer, R. A.; Tull, R. J. Org. Chem. 1978, 43, 509.
    • (1988) J. Org. Chem. , vol.53 , pp. 5994
    • Klein, R.F.X.1    Bargas, L.M.2    Horak, V.3
  • 11
    • 0017882651 scopus 로고
    • Corey E. J.; Achiwa, K. J. Am. Chem. Soc. 1969, 91, 1429. For further studies with quinone 13, see: Klein, R. F. X.; Bargas, L. M.; Horak, V. J. Org. Chem. 1988, 53, 5994. Vander Zwan, M. C.; Hartner, F. W.; Reamer, R. A.; Tull, R. J. Org. Chem. 1978, 43, 509.
    • (1978) J. Org. Chem. , vol.43 , pp. 509
    • Vander Zwan, M.C.1    Hartner, F.W.2    Reamer, R.A.3    Tull, R.4
  • 15
    • 0029148770 scopus 로고
    • Mure, M.; Klinman, J. P. J. Am. Chem. Soc. 1995, 117, 8698 and 8707. Lee, Y.; Sayre, L. M. J. Am. Chem. Soc. 1995, 117, 11823.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 8698
    • Mure, M.1    Klinman, J.P.2
  • 16
    • 0029176473 scopus 로고
    • Mure, M.; Klinman, J. P. J. Am. Chem. Soc. 1995, 117, 8698 and 8707. Lee, Y.; Sayre, L. M. J. Am. Chem. Soc. 1995, 117, 11823.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 11823
    • Lee, Y.1    Sayre, L.M.2
  • 17
    • 16044372469 scopus 로고    scopus 로고
    • note
    • The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK. We wish to thank J. Fraanje, K. Goubitz, and H. Schenk of the Department of Crystallography of this University for the X-ray crystal structure determination of compound 21.
  • 19
    • 0025942879 scopus 로고
    • Recent syntheses of lupinamine: (a) Wanner, M. J.; Koomen G.-J. Tetrahedron 1991, 47, 8431. (b) Michael, J. P.; Jungmann, C. M. Tetrahedron 1992, 48, 10211.
    • (1991) Tetrahedron , vol.47 , pp. 8431
    • Wanner, M.J.1    Koomen, G.-J.2
  • 20
    • 0026574828 scopus 로고
    • Recent syntheses of lupinamine: (a) Wanner, M. J.; Koomen G.-J. Tetrahedron 1991, 47, 8431. (b) Michael, J. P.; Jungmann, C. M. Tetrahedron 1992, 48, 10211.
    • (1992) Tetrahedron , vol.48 , pp. 10211
    • Michael, J.P.1    Jungmann, C.M.2
  • 22
    • 16044370072 scopus 로고
    • Mothes, K., Schütte, H. R., Luckner, M., Eds.; VCH publishers: Deerfield Beach
    • (b) Gross, D. In Biochemistry of Alkaloids; Mothes, K., Schütte, H. R., Luckner, M., Eds.; VCH publishers: Deerfield Beach, 1985; p 163.
    • (1985) Biochemistry of Alkaloids , pp. 163
    • Gross, D.1
  • 23
  • 26
    • 6444228635 scopus 로고
    • The corresponding symmetric trimer of 1 is an easy to handle, crystalline substance. Dissolving this trimer in dilute HCl results in a rapid hydrolysis to the protonated monomeric form of 1: (a) Schöpf, C.; Braun, F.; Komzak, A. Chem. Ber. 1956, 89, 1821. (b) Wanner, M. J.; Velzel, A. W.; Koomen, G.-J. J. Chem. Soc., Chem. Commun. 1993, 174.
    • (1956) Chem. Ber. , vol.89 , pp. 1821
    • Schöpf, C.1    Braun, F.2    Komzak, A.3
  • 27
    • 0027412626 scopus 로고
    • The corresponding symmetric trimer of 1 is an easy to handle, crystalline substance. Dissolving this trimer in dilute HCl results in a rapid hydrolysis to the protonated monomeric form of 1: (a) Schöpf, C.; Braun, F.; Komzak, A. Chem. Ber. 1956, 89, 1821. (b) Wanner, M. J.; Velzel, A. W.; Koomen, G.-J. J. Chem. Soc., Chem. Commun. 1993, 174.
    • (1993) J. Chem. Soc., Chem. Commun. , pp. 174
    • Wanner, M.J.1    Velzel, A.W.2    Koomen, G.-J.3
  • 28
    • 16044374312 scopus 로고    scopus 로고
    • note
    • 13C NMR only C3 of the piperidine ring was double (Δδ = 0.08 ppm).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.