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Volumn 69, Issue 6, 2004, Pages 1794-1799

Synthesis of the Aziridinomitosene Skeleton by Intramolecular Michael Addition of α-Lithioaziridines: An Aromatic Route Featuring Deuterium as a Removable Blocking Group

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; DEUTERIUM; ESTERS; LITHIUM; REDUCTION; SYNTHESIS (CHEMICAL);

EID: 1642330885     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030223i     Document Type: Article
Times cited : (32)

References (70)
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    • (1974) J. Org. Chem. , vol.39 , pp. 1192
    • Knaus, G.1    Meyers, A.I.2
  • 56
    • 0029822037 scopus 로고    scopus 로고
    • (a) Knaus, G.; Meyers, A. I. J. Org. Chem. 1974, 39, 1192. Warmus, J. S. ; Rodkin, M. A.; Barkley, R.; Meyers, A. I. J. Chem. Soc., Chem. Commun. 1993, 1357. Kopach, M. E.; Meyers, A. I. J. Org. Chem. 1996, 61, 6764.
    • (1996) J. Org. Chem. , vol.61 , pp. 6764
    • Kopach, M.E.1    Meyers, A.I.2
  • 57
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    • (b) Clive, D. L. J.; Khodabocus, A.; Cantin, M.; Tao, Y. J. Chem. Soc., Chem. Commun. 1991, 1755. Clive, D. L. J.; Cantin, M.; Khodabocus, A.; Kong, X. ; Tao, Y. Tetrahedron 1993, 49, 7917. Clive, D. L. J.; Tao, Y.; Khodabocus, A.; Wu, Y.-J.; Angoh, A. G.; Bennett, S. M.; Boddy, C. N.; Bordeleau, L.; Kellner, D.; Kleiner, G.; Middleton, D. S.; Nichols, C. J.; Richardson, S. R.; Vernon, P. G. J. Am. Chem. Soc. 1994, 116, 11275.
    • (1991) J. Chem. Soc., Chem. Commun. , pp. 1755
    • Clive, D.L.J.1    Khodabocus, A.2    Cantin, M.3    Tao, Y.4
  • 58
    • 0027292554 scopus 로고
    • (b) Clive, D. L. J.; Khodabocus, A.; Cantin, M.; Tao, Y. J. Chem. Soc., Chem. Commun. 1991, 1755. Clive, D. L. J.; Cantin, M.; Khodabocus, A.; Kong, X. ; Tao, Y. Tetrahedron 1993, 49, 7917. Clive, D. L. J.; Tao, Y.; Khodabocus, A.; Wu, Y.-J.; Angoh, A. G.; Bennett, S. M.; Boddy, C. N.; Bordeleau, L.; Kellner, D.; Kleiner, G.; Middleton, D. S.; Nichols, C. J.; Richardson, S. R.; Vernon, P. G. J. Am. Chem. Soc. 1994, 116, 11275.
    • (1993) Tetrahedron , vol.49 , pp. 7917
    • Clive, D.L.J.1    Cantin, M.2    Khodabocus, A.3    Kong, X.4    Tao, Y.5
  • 66
    • 1642299230 scopus 로고    scopus 로고
    • note
    • The sulfide series corresponding to the sulfone was also briefly investigated. No cyclization products were detected upon tin-lithium exchange, and destannylation was the exclusive pathway.
  • 68
    • 1642388753 scopus 로고    scopus 로고
    • note
    • According to NMR comparisons, structure 37 is identical with the major component obtained by Michael et al. using a different approach (ref 22). We thank Dr. Michael for providing copies of the NMR spectra.


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