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Volumn , Issue 14, 2009, Pages 2418-2422

Concise total synthesis of (+)-disparlure and its trans-isomer using asymmetric organocatalysis

Author keywords

Asymmetric synthesis; Disparlure; Olefin cross metathesis; Organocatalysis; Total synthesis

Indexed keywords

ASYMMETRIC SYNTHESIS; DISPARLURE; OLEFIN CROSS METATHESIS; ORGANOCATALYSIS; TOTAL SYNTHESIS;

EID: 67651112161     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216855     Document Type: Article
Times cited : (27)

References (35)
  • 6
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    • For recent syntheses of disparlure, see: a
    • For recent syntheses of disparlure, see: (a) Prasad, K. R.; Anbarasan, P. J. Org. Chem. 2007, 72, 3155.
    • (2007) J. Org. Chem , vol.72 , pp. 3155
    • Prasad, K.R.1    Anbarasan, P.2
  • 21
    • 34250684250 scopus 로고    scopus 로고
    • For a review on total synthesis based on asymmetric organocatalysis, see
    • (d) For a review on total synthesis based on asymmetric organocatalysis, see: de Figueiredo, R. M.; Christmann, M. Eur. J. Org. Chem. 2007, 2575.
    • (2007) Eur. J. Org. Chem , pp. 2575
    • de Figueiredo, R.M.1    Christmann, M.2
  • 23
    • 0041733541 scopus 로고    scopus 로고
    • For selected examples of proline-catalyzed asymmetric aaminoxylation of aldehydes, see: a
    • For selected examples of proline-catalyzed asymmetric aaminoxylation of aldehydes, see: (a) Brown, S. P.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 10808.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 10808
    • Brown, S.P.1    Brochu, M.P.2    Sinz, C.J.3    MacMillan, D.W.C.4
  • 26
    • 0029933487 scopus 로고    scopus 로고
    • 6b,7 (2:3, anti/syn, in our cases) comes from the use of different aldehyde substrates, not a solvent effect. The major isomer could be inverted according to the substrates used in the indium-mediated allylation of a-oxygenated aldehydes; see: Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931.
    • 6b,7 (2:3, anti/syn, in our cases) comes from the use of different aldehyde substrates, not a solvent effect. The major isomer could be inverted according to the substrates used in the indium-mediated allylation of a-oxygenated aldehydes; see: Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931.
  • 27
    • 0001712918 scopus 로고    scopus 로고
    • For selected articles on olefin cross metathesis, see: a
    • For selected articles on olefin cross metathesis, see: (a) Cossy, J.; BouzBouz, S.; Hoveyda, A. H. J. Organomet. Chem. 2001, 624, 327.
    • (2001) J. Organomet. Chem , vol.624 , pp. 327
    • Cossy, J.1    BouzBouz, S.2    Hoveyda, A.H.3
  • 30
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    • 13C NMR spectroscopy, was not important because the double bond was reduced by hydrogenation in the next step.
    • 13C NMR spectroscopy, was not important because the double bond was reduced by hydrogenation in the next step.
  • 32
    • 84886357323 scopus 로고    scopus 로고
    • We have found that Grubbs' catalyst cleanly cleaved the N-O bond of 4 to furnish diol in the case of the absence of a cross-metathesis partner; detailed results will be published in due course
    • We have found that Grubbs' catalyst cleanly cleaved the N-O bond of 4 to furnish diol in the case of the absence of a cross-metathesis partner; detailed results will be published in due course.
  • 33
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    • For an example of the use of Grubbs' catalyst as a reagent for N-deallylation, see
    • For an example of the use of Grubbs' catalyst as a reagent for N-deallylation, see: Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Org. Lett. 2001, 3, 3781.
    • (2001) Org. Lett , vol.3 , pp. 3781
    • Alcaide, B.1    Almendros, P.2    Alonso, J.M.3    Aly, M.F.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.