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Volumn 8, Issue 14, 2006, Pages 2985-2988

Stereoselective synthesis of pyridinones: Application to the synthesis of (-)-barrenazines

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BARRENAZINE A; BARRENAZINE B; FUSED HETEROCYCLIC RINGS; PYRIDINIUM DERIVATIVE; PYRIDONE DERIVATIVE;

EID: 33746658046     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0609006     Document Type: Article
Times cited : (79)

References (53)
  • 5
    • 0842268019 scopus 로고    scopus 로고
    • For recent reviews on the stereoselective synthesis of piperidines, see: (a) Buffat, M. G. P. Tetrahedron 2004, 60, 1701-1729.
    • (2004) Tetrahedron , vol.60 , pp. 1701-1729
    • Buffat, M.G.P.1
  • 8
    • 28244457575 scopus 로고    scopus 로고
    • For selected, recent references on the syntheses of pyridinones by addition of nucleophiles to pyridinium salts and the use of pyridinones in synthesis, see: (a) Comins, D. L.; Sahn, J. J. Org. Lett. 2005, 7, 5227-5228.
    • (2005) Org. Lett. , vol.7 , pp. 5227-5228
    • Comins, D.L.1    Sahn, J.J.2
  • 19
    • 33746657396 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details.
  • 20
    • 33746614935 scopus 로고    scopus 로고
    • note
    • 2. See Supporting Information for details.
  • 21
    • 33746625358 scopus 로고    scopus 로고
    • note
    • THF had to be added in these reactions to solubilize the organomagnesium reagents.
  • 27
    • 0000365487 scopus 로고    scopus 로고
    • For review of β-iodo carbonyl compounds in Pd-catalyzed cross-coupling reactions, see: Negishi, E. J. Organomet. Chem. 1999, 576, 179-194.
    • (1999) J. Organomet. Chem. , vol.576 , pp. 179-194
    • Negishi, E.1
  • 46
    • 33748542524 scopus 로고
    • (c) Johnson, F. Chem. Rev. 1968, 68, 375-413. See also the X-ray crystal structures in the Supporting Information.
    • (1968) Chem. Rev. , vol.68 , pp. 375-413
    • Johnson, F.1
  • 47
    • 33746603274 scopus 로고    scopus 로고
    • note
    • The ratio of barrenazine/TFA was determined by NMR using α,α,α-trifluorotoluene as the internal standard.
  • 48
    • 2942589152 scopus 로고    scopus 로고
    • For reviews on the olefin metathesis reaction, see: (a) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238.
    • (2004) Chem. Rev. , vol.104 , pp. 2199-2238
    • Deiters, A.1    Martin, S.F.2
  • 49
  • 53
    • 33746648840 scopus 로고    scopus 로고
    • note
    • A mixture of E/Z double-bond isomers in a ratio of 8:1 is isolated, if the hydrogenation step is avoided.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.