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Volumn 72, Issue 4, 2007, Pages 1226-1234

Stereoselective synthesis of polyhydroxylated quinolizidines from C-glycosides by one-pot double-conjugate addition

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYLATION; KETONES; MOLECULAR DYNAMICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 33847005954     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062057v     Document Type: Article
Times cited : (21)

References (103)
  • 1
    • 26844582966 scopus 로고    scopus 로고
    • and previous reports from this author
    • Michael, J. P. Nat. Prod. Rep. 2005, 22, 603-626 and previous reports from this author.
    • (2005) Nat. Prod. Rep , vol.22 , pp. 603-626
    • Michael, J.P.1
  • 13
    • 22244454093 scopus 로고    scopus 로고
    • For examples, see: a
    • For examples, see: (a) Maloney, K. M.; Danheiser, R. L. Org. Lett. 2005, 7, 3115-3118.
    • (2005) Org. Lett , vol.7 , pp. 3115-3118
    • Maloney, K.M.1    Danheiser, R.L.2
  • 27
    • 0035944143 scopus 로고    scopus 로고
    • Broggini, G.; La, Rosa, C.; Pilati, T.; Terraneo, A.; Zecchi, G. Tetrahedron 2001, 57, 8323-8332.
    • (b) Broggini, G.; La, Rosa, C.; Pilati, T.; Terraneo, A.; Zecchi, G. Tetrahedron 2001, 57, 8323-8332.
  • 36
    • 0034721683 scopus 로고    scopus 로고
    • (a) Nemr, A. L. Tetrahedron 2000, 56, 8579-8629.
    • (2000) Tetrahedron , vol.56 , pp. 8579-8629
    • Nemr, A.L.1
  • 47
    • 0028853464 scopus 로고    scopus 로고
    • Herczegh, P.; Kovács, I.; Szilágyi, L.; Sztaricskaia, F.; Amaya, Berecibar, A.; Claude, Riche, C.; Chiaroni, A.; Olesker, A.; Lukacs, G. Tetrahedron 1995, 51, 2969-2978.
    • Herczegh, P.; Kovács, I.; Szilágyi, L.; Sztaricskaia, F.; Amaya, Berecibar, A.; Claude, Riche, C.; Chiaroni, A.; Olesker, A.; Lukacs, G. Tetrahedron 1995, 51, 2969-2978.
  • 61
    • 0000679263 scopus 로고    scopus 로고
    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer: Berlin, Chapter 31.1
    • (c) Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, Chapter 31.1.
    • (1999) Comprehensive Asymmetric Catalysis , vol.3
    • Tomioka, K.1    Nagaoka, Y.2
  • 62
    • 0003913629 scopus 로고    scopus 로고
    • Otera, J, Ed, Wiley-VCH: Weinheim, Chapter 12
    • (d) Tomioka, K. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 12.
    • (2000) Modern Carbonyl Chemistry
    • Tomioka, K.1
  • 65
    • 0028130028 scopus 로고
    • (a) Cole, D. C. Tetrahedron 1994, 50, 9517-9582.
    • (1994) Tetrahedron , vol.50 , pp. 9517-9582
    • Cole, D.C.1
  • 90
    • 33846949923 scopus 로고    scopus 로고
    • To avoid confusion in the assignment of NMR data the carbon numbering used in this paper corresponds to the numbering of the original carbohydrates
    • To avoid confusion in the assignment of NMR data the carbon numbering used in this paper corresponds to the numbering of the original carbohydrates.
  • 91
    • 33847005292 scopus 로고    scopus 로고
    • Better yield might be obtainable by stoicheiometric reaction of freshly prepared AllylMgBr with azidoaldehyde
    • Better yield might be obtainable by stoicheiometric reaction of freshly prepared AllylMgBr with azidoaldehyde.
  • 94
    • 33846995862 scopus 로고    scopus 로고
    • In the previous report (ref 20, we presumed a similar L-arabinoazasugar adopting 4C1 conformation (equatorial orientation at C2 and C3 and axial at C4) and thus made an error in the assignment of the anomeric stereochemistry
    • 1 conformation (equatorial orientation at C2 and C3 and axial at C4) and thus made an error in the assignment of the anomeric stereochemistry.
  • 95
    • 0001258881 scopus 로고    scopus 로고
    • It is noteworthy that the hydroxylated quinolizidines 9, 20, and 21 described here possess the same or similar skeleton as naturally occurring myrtine from plants and xestosin found from marine sponges. See: (a) Slosse, P.; Hootelé, C. Tetrahedron 1981, 37, 4287-4294.
    • It is noteworthy that the hydroxylated quinolizidines 9, 20, and 21 described here possess the same or similar skeleton as naturally occurring myrtine from plants and xestosin found from marine sponges. See: (a) Slosse, P.; Hootelé, C. Tetrahedron 1981, 37, 4287-4294.
  • 97
    • 33846998864 scopus 로고    scopus 로고
    • We attempted to record NMR spectra at 60°C; unfortunately, epimerization at C4′ likely occurred in both 20 and 21, as indicated by the proportional decrease of 4′-Me signals of 20 and 21 and by the appearance of a methyl resonance at 1.24 ppm J, 5.9 Hz, See ref 32a
    • We attempted to record NMR spectra at 60°C; unfortunately, epimerization at C4′ likely occurred in both 20 and 21, as indicated by the proportional decrease of 4′-Me signals of 20 and 21 and by the appearance of a methyl resonance at 1.24 ppm (J = 5.9 Hz). See ref 32a.
  • 98
    • 33646469767 scopus 로고    scopus 로고
    • The conformation should unlikely be affected by the stereoelectronic substituent effects which were observed upon protonation of azasugars. See: (a) Jensen, H. H, Bols, M. Acc. Chem. Res. 2006, 39, 259-265
    • The conformation should unlikely be affected by the stereoelectronic substituent effects which were observed upon protonation of azasugars. See: (a) Jensen, H. H.; Bols, M. Acc. Chem. Res. 2006, 39, 259-265.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.