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Volumn 63, Issue 22, 1998, Pages 7953-7956

Internal Diels-Alder Cycloaddition with a Z-Dienophile: Synthesis of (±)-α-Oplopenone

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EID: 0001427718     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981248y     Document Type: Article
Times cited : (15)

References (44)
  • 10
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    • Trost, B. M., Fleming, I., Eds.; Pergamon: New York
    • (j) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1992; Vol. 5, p 513.
    • (1992) Comprehensive Organic Synthesis , vol.5 , pp. 513
    • Roush, W.R.1
  • 11
    • 0025870111 scopus 로고
    • For more recent examples of internal Diels-Alder cycloadditions, see: (a) Wilson, S. R.; Di Grandi, M. J. J. Org. Chem. 1991, 56, 4766.
    • (1991) J. Org. Chem. , vol.56 , pp. 4766
    • Wilson, S.R.1    Di Grandi, M.J.2
  • 27
    • 33746558973 scopus 로고
    • No synthetic efforts toward α-oplopenone had been described prior to the work reported here.
    • For the isolation and structural determination of α-oplopenone, see: De Pascale-T., J.; Vicente, S.; Gonzalez, M. S.; Bellido, I. S. Phytochemistry 1983,22, 2235. No synthetic efforts toward α-oplopenone had been described prior to the work reported here.
    • (1983) Phytochemistry , vol.22 , pp. 2235
    • De Pascale-T, J.1    Vicente, S.2    Gonzalez, M.S.3    Bellido, I.S.4
  • 31
    • 33744881588 scopus 로고    scopus 로고
    • A more straightforward variation would be to condense the enolate of 5 with nitrile 4 to give the diketone 6 directly. Our repeated attempts to effect such a condensation were unfortunately unavailing.
    • A more straightforward variation would be to condense the enolate of 5 with nitrile 4 to give the diketone 6 directly. Our repeated attempts to effect such a condensation were unfortunately unavailing.
  • 35
    • 0000085217 scopus 로고
    • For a synthesis of authentic chiloscyphone, see: Piers, E.; Tse, H. L. A. Can. J. Chem. 1993, 71, 983.
    • (1993) Can. J. Chem. , vol.71 , pp. 983
    • Piers, E.1    Tse, H.L.A.2
  • 38
    • 0001078061 scopus 로고
    • For leading references to alternative strategies for the one-carbon homologation of an acid or ester to the methyl ketone see
    • (b) Chou, T.-S.; Huang, S.-B. Tetrahedron Lett. 1983, 24, 2169. For leading references to alternative strategies for the one-carbon homologation of an acid or ester to the methyl ketone see:
    • (1983) Tetrahedron Lett. , vol.24 , pp. 2169
    • Chou, T.-S.1    Huang, S.-B.2
  • 42
    • 0028344377 scopus 로고
    • For leading references to the analogous homologation of amides, see
    • (f) Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994,35,1669. For leading references to the analogous homologation of amides, see:
    • (1994) Tetrahedron Lett. , vol.35 , pp. 1669
    • Cook, G.R.1    Beholz, L.G.2    Stille, J.R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.