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Volumn 75, Issue 3, 2010, Pages 815-824

Total synthesis of uniflorine A, casuarine, australine, 3-epi-australine, and 3,7-di-epi-australine from a common precursor

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; DIASTEREOSELECTIVE; DIHYDROPYRROLE; PYRROLIZIDINE ALKALOID; TOTAL SYNTHESIS;

EID: 75749099813     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902355p     Document Type: Article
Times cited : (92)

References (54)
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    • For a preliminary communication on the synthesis of, -uniflorine
    • For a preliminary communication on the synthesis of (+)-uniflorine A, see: Ritthiwigrom, T.; Pyne, S. G. Org. Lett. 2008, 10, 2769-2771.
    • (2008) Org. Lett , vol.10 , pp. 2769-2771
    • see, A.1    Ritthiwigrom, T.2    Pyne, S.G.3
  • 7
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    • Fattorusso, E, Taglialatela-Scafati, O, Eds, Wiley-VCH Verlag: Weinheim, Germany
    • Asano, N. In Modern Alkaloids: Structure, Isolation, Synthesis and Biology; Fattorusso, E., Taglialatela-Scafati, O., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 2008; pp 111-138.
    • (2008) Modern Alkaloids: Structure, Isolation, Synthesis and Biology , pp. 111-138
    • Asano, N.1
  • 17
    • 0033592505 scopus 로고    scopus 로고
    • For previous syntheses of casuarine see
    • For previous syntheses of casuarine see: Denmark, S. E.; Hurd, A. R. Org. Lett. 1999, 1, 1311-1314.
    • (1999) Org. Lett , vol.1 , pp. 1311-1314
    • Denmark, S.E.1    Hurd, A.R.2
  • 20
    • 60749132180 scopus 로고    scopus 로고
    • Cardona, F.; Parmeggiani1, C.; Faggi, E.; Bonaccini, C.; Gratteri, P.; Sim, L.; Gloster, T. M.; Roberts, S.; Davies, G. J.; Rose, D. R.; Goti, A. Chem.;Eur. J. 2009, 15, 1627-1636.
    • Cardona, F.; Parmeggiani1, C.; Faggi, E.; Bonaccini, C.; Gratteri, P.; Sim, L.; Gloster, T. M.; Roberts, S.; Davies, G. J.; Rose, D. R.; Goti, A. Chem.;Eur. J. 2009, 15, 1627-1636.
  • 21
    • 0025943456 scopus 로고
    • For previous syntheses of australine see: a
    • For previous syntheses of australine see: (a) Pearson, W. H.; Hines, J. V. Tetrahedron Lett. 1991, 32, 5513-5516.
    • (1991) Tetrahedron Lett , vol.32 , pp. 5513-5516
    • Pearson, W.H.1    Hines, J.V.2
  • 29
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    • For a synthesis of australine from castanospermine see
    • (i) For a synthesis of australine from castanospermine see: Furneaux, R. H.; Gainsford,G. J.; Mason, J. M.; Tyler, P. C. Tetrahedron 1994, 50, 2131-2160.
    • (1994) Tetrahedron , vol.50 , pp. 2131-2160
    • Furneaux, R.H.1    Gainsford, G.J.2    Mason, J.M.3    Tyler, P.C.4
  • 30
    • 75749085533 scopus 로고    scopus 로고
    • For previous syntheses of 3-epi-australine see: refs 14c and 14f.
    • For previous syntheses of 3-epi-australine see: refs 14c and 14f.
  • 42
    • 75749158288 scopus 로고    scopus 로고
    • Unfortunately we have not been able to obtain a copy of the NMR spectra of uniflorine A for comparison purposes from the original authors.1
    • 1
  • 44
    • 75749114917 scopus 로고    scopus 로고
    • Crystal/refinement data have been deposited with the Cambridge Crystallographic Data Centre as CCDC 752850
    • Crystal/refinement data have been deposited with the Cambridge Crystallographic Data Centre as CCDC 752850.
  • 50
    • 75749127586 scopus 로고    scopus 로고
    • 13CNMR chemical shifts for natural and synthetic australine see the Supporting Information in ref 14g.
    • 13CNMR chemical shifts for natural and synthetic australine see the Supporting Information in ref 14g.
  • 52
    • 54049118080 scopus 로고    scopus 로고
    • For a flexible synthetic strategy for preparing several hyacinthacine alkaloids and epimers and 2,3,7-tri-epi-australine see: Donohoe, T. J.; Thomas, R. E.; Cheeseman, M. D.; Rigby, C. L.; Bhalay, G.; Linney, I. D. Org. Lett. 2008, 10, 3615-3618.
    • For a flexible synthetic strategy for preparing several hyacinthacine alkaloids and epimers and 2,3,7-tri-epi-australine see: Donohoe, T. J.; Thomas, R. E.; Cheeseman, M. D.; Rigby, C. L.; Bhalay, G.; Linney, I. D. Org. Lett. 2008, 10, 3615-3618.
  • 53
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    • After submission of this manuscript an alternative synthesis of uniflorine A was published, see
    • After submission of this manuscript an alternative synthesis of uniflorine A was published, see: Parmeggiani, C.; Martella, D.; Cardona, F.; Goti, A. J. Nat. Prod. 2009, 72, 2058-2060.
    • (2009) J. Nat. Prod , vol.72 , pp. 2058-2060
    • Parmeggiani, C.1    Martella, D.2    Cardona, F.3    Goti, A.4
  • 54
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    • 3 solution unless otherwise indicated. NMR assignments are based upon COSY and HSQC, and sometimes HMBC and NOESY, NMR experiments. All IR spectra were run on neat samples.
    • 3 solution unless otherwise indicated. NMR assignments are based upon COSY and HSQC, and sometimes HMBC and NOESY, NMR experiments. All IR spectra were run on neat samples.


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