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Volumn 51, Issue 43, 1995, Pages 11703-11724

Total syntheses of the metabolites of schizandrin

Author keywords

[No Author keywords available]

Indexed keywords

DRUG METABOLITE; LIGNAN; SCHIZANDRIN;

EID: 0028864840     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00702-A     Document Type: Article
Times cited : (26)

References (48)
  • 11
    • 0011831846 scopus 로고
    • First Total Synthesis of Optically Pure Metabolites of Gomisin A
    • The syntheses of the structurally related metabolites of gomisin A:
    • (1994) Synlett , pp. 604
    • Tanaka1    Mitsuhashi2    Maruno3    Wakamatsu4
  • 42
    • 84916468177 scopus 로고    scopus 로고
    • 2 (1:10), the progress of the reaction was very sluggish.
  • 43
    • 0003002042 scopus 로고
    • A new and facile method for the direct preparation of .ALPHA.-hydroxycarboxylic acid esters from .ALPHA.,.BETA.-unsaturated carboxylic acid esters with moleciular oxygen and phenylsilane catalyzed by bis(dipivaloymethanato)manganese(II) complex.
    • and references cited therein.
    • (1990) Chemistry Letters , pp. 1869
    • Inoki1    Kato2    Isayama3    Mukaiyama4
  • 44
    • 2742522130 scopus 로고
    • The Migration of Double Bond under the Neutral Conditions. The Transformation of .ALPHA.-Alkylidene Cyclic Carbonyl Compounds to .ALPHA.,.BETA.-Unsaturated Cyclic Carbonyl Compounds.
    • (1994) Chemistry Letters , pp. 1455
    • Tanaka1    Mitsuhashi2    Maruno3    Wakamatsu4
  • 45
    • 84916522963 scopus 로고    scopus 로고
    • 3) δ: 2.94 (1H, d, J = 16 Hz), 2.90–3.14 (2H, m), 3.55 (1H, d, J = 11 Hz), 3.70 (3H, s), 3.84 (3H, s), 3.88 (3H, s), 3.90 (3H, s), 3.93 (3H, s), 4.65 (2H, d, J = 3 Hz), 4.77 (1H, d, J = 11 Hz), 5.03 (1H, d, J = 11 Hz), 6.41 (1H, s), 6.59 (1H, s), 6.99–7.04 [[Truncated]]
  • 46
    • 84916484118 scopus 로고    scopus 로고
    • 3) δ: 1.86 (1H, br), 2.10- 2.30 (1H, m), 2.57 (1H, d, J = 13 Hz), 2.73 (1H, dd, J = 12, 15 Hz), 3.01 (1H, dd, J = 7, 15 Hz), 3.44 (1H, d, J = 13 Hz), 3.57 (3H, s), 3.72 (3H, s), 3.84 (3H, s), 3.88 (3H, s), 3.89 (6H, s), 4.05 (1H, dd, J = 8, 10 Hz), 4.19 (1H, t, J = 8 Hz), 6.41 (1H, s), 6.55 (1H, s). See ref. 5n.
  • 48
    • 84916504619 scopus 로고    scopus 로고
    • Melting Points were measured using Buchi 535 melting point apparatus and are not corrected. Optical rotations were taken with a JASCO DIP-360 polarimeter. Ir spectra (IR) were obtained with a Hitachi 270-30 spectrophotometer. NMR spectra were measured in deuteriochloroform with a JEOL FX-200 Spectrometer at 200 MHz. Chemical shift values are expressed in ppm relative to internal tetramethylsilane. Abbreviations are as follows: s, singlet; t, triplet; q, quartet; m, multiplet; br, broad. Mass spectra (MS) and high resolution mass spectra (HRMS) were measured with a KRATOS CONCEPT 32 1H and 1S mass spectrometers. Flash chromatography was performed with silica gel 60 (230–400 mesh).


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