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Volumn 46, Issue 28, 2005, Pages 4719-4722

A novel approach to functionalized (E)-1,4-diaryl-1-butenes by Heck reaction and their applications for the construction of dibenzylbutyrolactone lignan skeletons by radical cyclization

Author keywords

Dibenzylbutyrolactones; Heck reaction; Radical cyclization; Stereoselective synthesis; Styrene derivatives

Indexed keywords

ALKENYL GROUP; FLUORIDE; LACTONE DERIVATIVE; LIGNAN DERIVATIVE; RADICAL; STYRENE DERIVATIVE;

EID: 20444397378     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.050     Document Type: Article
Times cited : (16)

References (29)
  • 2
    • 0000351132 scopus 로고    scopus 로고
    • Lignans: Biosynthesis and Function
    • U. Sankura Elsevier Amsterdam
    • N.G. Lewis, and L.B. Davis U. Sankura Lignans: Biosynthesis and Function Comprehensive Natural Product Chemistry Vol. 1 1999 Elsevier Amsterdam 639 712
    • (1999) Comprehensive Natural Product Chemistry , vol.1 , pp. 639-712
    • Lewis, N.G.1    Davis, L.B.2
  • 3
    • 77957069771 scopus 로고    scopus 로고
    • Recent Advances in the Chemistry of Lignans
    • A.U. Rahman Studies in Natural Products Chemistry Elsevier Amsterdam
    • R.S. Ward Recent Advances in the Chemistry of Lignans A.U. Rahman Studies in Natural Products Chemistry Bioactive Natural Products, Part E Vol. 24 2000 Elsevier Amsterdam 739 798 and references cited therein
    • (2000) Bioactive Natural Products, Part e , vol.24 , pp. 739-798
    • Ward, R.S.1
  • 11
    • 0036399126 scopus 로고    scopus 로고
    • The direct cross-coupling of alkenyl(phenyl)silane via an alkenylsilanol with iodobenzene to produce a cine-coupled product has been reported. See: J.C. Anderson, S. Anguille, and R. Bailey Chem. Commun. 2002 2018 2019
    • (2002) Chem. Commun. , pp. 2018-2019
    • Anderson, J.C.1    Anguille, S.2    Bailey, R.3
  • 16
    • 20444394853 scopus 로고    scopus 로고
    • note
    • Increasing the reaction temperature in the range of 40-80°C did not improve the yield; instead, by products were formed
  • 18
    • 20444404730 scopus 로고    scopus 로고
    • note
    • 3P in the presence and absence of TBAF at 80°C, but the conversion was <5% in both the cases
  • 19
    • 20444392477 scopus 로고    scopus 로고
    • note
    • 2 (48 mg, 0.13 mmol) were added and the mixture was heated at 80°C under a blanket of nitrogen in a Schlenk flask for 40 h. The reaction mixture was cooled, diluted with hexane-EtOAc (8/2) and washed with water. The organic extract was concentrated and purified by column chromatography to give 1a (760 mg, 75%) as a colourless oil
  • 20
    • 20444368138 scopus 로고    scopus 로고
    • note
    • The products were fully characterized by physical and spectroscopic data. Compounds 1a-1f and 7a-7e gave satisfactory analytical (CHN) data. The compositions of 1g, 1h, 3c and 4c were confirmed by ESI-HRMS measurements
  • 21
    • 20444420986 scopus 로고    scopus 로고
    • note
    • The products were fully characterized by physical and spectroscopic data. Compounds 8, cis-10 and trans-10 gave satisfactory analytical (CH) data. The composition of 11 was confirmed by ESI-HRMS measurement
  • 22
    • 84970544676 scopus 로고
    • The corresponding methylthiomethyl and phenylthiomethyl esters did not undergo radical cyclization smoothly; see: A.L.J. Beckwith, and P.E. Pigou Aust. J. Chem. 39 1986 77 87
    • (1986) Aust. J. Chem. , vol.39 , pp. 77-87
    • Beckwith, A.L.J.1    Pigou, P.E.2
  • 23
    • 20444403982 scopus 로고    scopus 로고
    • note
    • 3) δ 30.76, 31.94, 39.95, 45.17, 55.20, 69.36, 114.06 (2C), 126.63, 128.33 (2C), 128.73 (2C), 129.84 (2C), 130.30, 138.58, 158.27, 177.93
  • 26
    • 20444395920 scopus 로고    scopus 로고
    • note
    • Obtained as inseparable mixture of isomers


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