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Agricultural chemistry & biotechnology v.48 no.2, 2005년, pp.97 - 100   피인용횟수: 1

Facial Synthesis of Versatile Chiral Norbornenes as Leukotriene D4 Antagonists from D-glucose

Lim, Yoong-Ho  
  • 초록

    Chiral dienophile 5 was synthesized from D-glucose by consecutive diisopropylidenation, partial deprotection, diol cleavage, and Wittig reactions. Under thermal conditions, asymmetric Diels-Alder reaction between chiral dienophile and cyclopentadiene gave four possible chiral norbornenes stereoisomers whose absolute configurations were determined through CADD and NMR.


  • 주제어

    Asymmetric reaction .   Chiral Dienophiles .   Diels-Alder reaction .   Stereochemistry.  

  • 참고문헌 (18)

    1. Effect of Saikosaponin-A, a triterpenoid glycoside, isolated from Bupueurum falcatum on experimental allergic asthma , Park, K.H.;Park, J.;Koh, D.;Lim, Y. , Phytotheraphy Research / v.16,pp.359-363,
    2. Anti-allergic activity of a disaccharide isolated from Sanguisorba officinalis , Park, K.H.;Koh, D.;Park, J.;Kim, K.;Lim, Y. , Phytotherapy Research / v.18,pp.658-662,
    3. Synthesis and biological activities of leukotriene D4 antagonists predicted from quantitatively structure-activity relationship calculation , Koh, D.;Park, K.H.;Lim, Y. , Agric. Chem. Biotechnol. / v.44,pp.35-38,
    4. Resveratrol derivatives showing the leukotriene D4 antagonism , Koh, D.;Park, K.H.;Lee, H.;Jung, J.;Lim, Y. , Agric. Chem. Biotechnol. / v.44,pp.32-34,
    5. Anti-allergic and anti-asthmatic activity of Helioscopinin-A, a polyphenol compound, isolated from Euphorbia helioscopia , Koh, D.;Park, K.H.;Lee, S.;Jung, I.;Kim, K.;M.;Lee, C.;Kim, K.;Lim, Y. , J Mocrobiol. Biotechnol. / v.11,pp.138-142,
    6. Anti-allergic compound with Leukotriene D4 Antagonism isolated from Puerariae radix , Koh, D.;Park, K.H.;Lim, Y. , J. Korean Soc. Agric. Chem. Biotechnol. / v.44,pp.38-39,
    7. Quantitatively Structure-activity Relationships to Develop Anti-asrhmatic Drugs , Koh, D.;Park, K.H.;Lee, H.;Jung, J.;Cho, S.K.;Lim, Y. , Agric. Chem. Biotechnol. / v.43,pp.277-280,
    8. Enantioselective synthesis of S-1452, an orally active potent thromboxane A2 receptor antagonist , Ohitani, E.;Matsuura, T.;Watanabe, F.;Narisada, M. , J. Org. Chem. / v.56,pp.2122-2127,
    9. A C-Glycoside route to leukotrienes , Rokach, J.;Lau, C.K.;Zambony, R.;Guindon, Y. , Tetrahedron Lett. / v.22,pp.6313-6316,
    10. Regio- and stereoselective ring openings of 3-aza-2-oxabicyclo[2.2.1]hept-5-ene systems with copper catalyst-modified grignard reagents: Application to the synthesis of an inhibitor of 5-lipoxygenase , Surman, M.D.;Mulvihill, M.J.;Miller, M.J. , J. Org. Chem. / v.67,pp.4115-4121,
    11. Rapid chromatographic technique for preparative separation with moderate resolution , Still, W.C.;Kahn, M.;Mitr, A. , J. Org. Chem. / v.43,pp.2923-2925,
    12. Methods in carbohydrate chemistry, vol. VI , Stevene, J.D. , / v.,pp.123-129,
    13. In Methods in carbohydrate chemistry, vol. II , Schmodt, O.T. , / v.,pp.318-325,
    14. General procedure for a one-pot oxidative cleavage/Wittig reaction of glycols , Dunlap, N.K.;Mergo, W.;Jones, J.M.;Carrick, D.A. , Tetrahedron Lett. / v.43,pp.3923-3925,
    15. Total synthesis of Griseolic acid derivatives from D-glucose , Tulshian, D.;Doll, R.;Stansberry, M.F. , J. Org. Chem. / v.56,pp.6819-6822,
    16. Stereocontrol in Diels-Alder cycloaddition to unsaturated sugars: Reactivities of acyclic 7-carbon trans dienophiles derived from aldopentoses , Horton, D.;Koh, D. , Carbohydr. Res. / v.250,pp.249-260,
    17. Diastereoselectivity of a [3+2] annulation. On the question of a dipole effect on a stereoselectivity of olefin addition , Trost, B.M.;Lynch, J.;Renaut, P. , Tetrahedron Lett. / v.26,pp.6313-6316,
    18. Stereocontrol in Diels-Alder cycloaddition to unsaturated sugars: Reactivities of cis dienophiles with cyclopentadiene , Horton, D.;Koh, D.;Takagi, Y. , Carbohydr. Res. / v.250,pp.261-274,
  • 이 논문을 인용한 문헌 (1)

    1. 2007. "" Journal of applied biological chemistry, 50(4): 296~300     

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