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Volumn 75, Issue 3, 2010, Pages 933-936

Oxazolone cycloadducts as heterocyclic scaffolds for alkaloid construction: Synthesis of (±)-2-epi-pumiliotoxin C

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDUCTS; DIELS-ALDER CYCLOADDITIONS; FUNCTIONALIZED; REGIO-SELECTIVE;

EID: 75749132415     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902172r     Document Type: Article
Times cited : (20)

References (34)
  • 4
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    • Daly, J. W.; Tokuyama, T.; Habermehl, G.; Karle, I. L.; B. Witkop, B. Liebigs Ann. Chem. 1969, 727, 198-204.
    • Daly, J. W.; Tokuyama, T.; Habermehl, G.; Karle, I. L.; B. Witkop, B. Liebigs Ann. Chem. 1969, 727, 198-204.
  • 10
    • 4544221712 scopus 로고    scopus 로고
    • Current Organic Chemistry
    • For reviews, see: a, Ed, Bentham Science Publishers: The Netherlands
    • For reviews, see: (a) Fearnley, S. P. Current Organic Chemistry; Vol. 8, Asymmetric Synthesis; Atta-Ur-Rahman, Ed.; Bentham Science Publishers: The Netherlands, 2004; pp 1289-1338;
    • (2004) Asymmetric Synthesis; Atta-Ur-Rahman , vol.8 , pp. 1289-1338
    • Fearnley, S.P.1
  • 19
    • 41049116667 scopus 로고    scopus 로고
    • For specific examples of α-substituents exerting similar stereocontrol in IMDA ofN-acyl systems, see: Friedrich, A.; Jainta, M.; Nising, C. F.; Bräse, S. Synlett 2008, 589-591. and ref 6a.
    • For specific examples of α-substituents exerting similar stereocontrol in IMDA ofN-acyl systems, see: Friedrich, A.; Jainta, M.; Nising, C. F.; Bräse, S. Synlett 2008, 589-591. and ref 6a.
  • 22
    • 75749136641 scopus 로고    scopus 로고
    • See the Supporting Information for details of structural assignment
    • See the Supporting Information for details of structural assignment.
  • 29
    • 41149157530 scopus 로고    scopus 로고
    • Imidazoylthiocarbonyl formation: Winbush, S-A. M.; Mergott, D. J.; Roush, W. R. J. Org. Chem. 2008, 73, 1818-1829.
    • (a) Imidazoylthiocarbonyl formation: Winbush, S-A. M.; Mergott, D. J.; Roush, W. R. J. Org. Chem. 2008, 73, 1818-1829.
  • 30
    • 34447301779 scopus 로고    scopus 로고
    • Deoxygenation: Chochrek, P.; Wicha, J. J. Org. Chem. 2007, 72, 5276-5284.
    • (b) Deoxygenation: Chochrek, P.; Wicha, J. J. Org. Chem. 2007, 72, 5276-5284.
  • 33
    • 75749098629 scopus 로고    scopus 로고
    • Other possible complications include rotamers of the acetamide and quadrupolar broadening by nitrogen. We are grateful to the two reviewers who suggested these additional phenomena
    • Other possible complications include rotamers of the acetamide and quadrupolar broadening by nitrogen. We are grateful to the two reviewers who suggested these additional phenomena.


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