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Volumn 60, Issue 24, 1995, Pages 7791-7795

Conformational Control in the Cyclization of an Unsaturated Vinyllithium: Synthesis of (±)-Laurene

Author keywords

[No Author keywords available]

Indexed keywords

LAURENE; SESQUITERPENE; UNCLASSIFIED DRUG;

EID: 0028785390     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00129a020     Document Type: Article
Times cited : (37)

References (51)
  • 1
    • 0001433726 scopus 로고
    • Coxon, J. M., Ed.; JAI Press: Greenwich, CT Mechanisms of Importance in Synthesis
    • Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms, Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, Mechanisms of Importance in Synthesis; pp 251-273.
    • (1994) Advances in Detailed Reaction Mechanisms , vol.3 , pp. 251-273
    • Bailey, W.F.1    Ovaska, T.V.2
  • 24
    • 0000976629 scopus 로고
    • For the synthesis of (±)-laurene, see: (a)
    • For the synthesis of (±)-laurene, see: (a) McMurry, J. E.; von Beroldingen, L. A. Tetrahedron 1974, 30, 2027.
    • (1974) Tetrahedron , vol.30 , pp. 2027
    • McMurry, J.E.1    von Beroldingen, L.A.2
  • 37
    • 84942752381 scopus 로고
    • Formal dehydrohalogenation is a potentially serious complication when vinyl bromides are treated with t-BuLi, and for this reason such reactions are often conducted at temperatures below -110 °C to minimize alkyne formation when THF is employed as solvent for the lithium-bromine exchange and references therein). The use of a solvent system containing diethyl ether rather than THF6 allows for the clean generation of vinyllithiums by lithium-bromine exchange at a moee experimentally convenient temperature of -78 °C
    • Formal dehydrohalogenation is a potentially serious complication when vinyl bromides are treated with t-BuLi, and for this reason such reactions are often conducted at temperatures below -110 °C to minimize alkyne formation when THF is employed as solvent for the lithium-bromine exchange (Neuman, H.; Seebach, D. Chem. Ber. 1978, 111, 2785 and references therein). The use of a solvent system containing diethyl ether rather than THF6 allows for the clean generation of vinyllithiums by lithium-bromine exchange at a moee experimentally convenient temperature of -78 °C.
    • (1978) Chem. Ber. , vol.111 , pp. 2785
    • Neuman, H.1    Seebach, D.2
  • 38
    • 0026040962 scopus 로고
    • The sluggish cyclization of 2 in the absence of TMEDA is consistent with similar observations made in the couree of the preparation the sterically crowded sesquiterpene (±)-cuparene via cyclization of an olefinic alkyllithium
    • The sluggish cyclization of 2 in the absence of TMEDA is consistent with similar observations made in the couree of the preparation the sterically crowded sesquiterpene (±)-cuparene via cyclization of an olefinic alkyllithium: Bailey, W. F.; Khanolkar, A. D. Tetrahedron 1991, 47, 7727.
    • (1991) Tetrahedron , vol.47 , pp. 7727
    • Bailey, W.F.1    Khanolkar, A.D.2
  • 41
    • 0000102694 scopus 로고
    • Abramovitch, R. A., Ed.; Plenum: New York Chapter 3
    • Surzur, J. M. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum: New York, 1982; Vol. 2, Chapter 3.
    • (1982) Reactive Intermediates , vol.2
    • Surzur, J.M.1
  • 42
    • 0001562822 scopus 로고
    • Hart, D. J. Science 1984, 223, 883.
    • (1984) Science , vol.223 , pp. 883
    • Hart, D.J.1
  • 46
    • 84986437005 scopus 로고
    • Molecular mechanics calculations weee performed using the MM2∗ parameters incorporated in the MacroModel program
    • Molecular mechanics calculations weee performed using the MM2∗ parameters incorporated in the MacroModel program: Richards, N. G. L.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
    • (1990) J. Comput. Chem. , vol.11 , pp. 440
    • Richards, N.G.L.1    Guida, W.C.2    Liskamp, R.3    Caufield, C.4    Chang, G.5    Hendrickson, T.6    Still, W.C.7
  • 48
    • 0007100920 scopus 로고
    • Wiley: New York Collect.
    • Adams, R.; Thai, A. F. Organic Synthesis, Wiley: New York, 1932; Collect. Vol. 1, p 107.
    • (1932) Organic Synthesis , vol.1 , pp. 107
    • Adams, R.1    Thai, A.F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.