메뉴 건너뛰기




Volumn 5, Issue 12, 2000, Pages 1386-1398

Study of stereoselectivity in organometallic additions to 1,2-O-isopropylidene-O-R-α-D-xylopentodialdo-1,4-furanose

Author keywords

Addition to carbonyl; Organometallic reagents; Stereoselectivity

Indexed keywords

FURAN DERIVATIVE; ORGANOMETALLIC COMPOUND; REAGENT;

EID: 0009352233     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/51201386     Document Type: Article
Times cited : (17)

References (23)
  • 1
    • 0010384048 scopus 로고
    • Novel bioactive styryl-lactones: Goniofufurone, goniopypyrone, and 8-acetylgoniotriol from Goniothalamus giganteus (Annonaceae). X-ray molecular structure of goniofufurone and of goniopypyrone
    • Fang, X.-p.; Anderson, J.E.; Chang, C.-j.; Fanwick, P.E.; McLaughlin, J.L. Novel Bioactive Styryl-lactones: Goniofufurone, Goniopypyrone, and 8-Acetylgoniotriol from Goniothalamus giganteus (Annonaceae). X-Ray Molecular Structure of Goniofufurone and of Goniopypyrone. J. Chem. Soc. Perkin 1 1990, 1655-1661.
    • (1990) J. Chem. Soc. Perkin 1 , pp. 1655-1661
    • Fang, X.-P.1    Anderson, J.E.2    Chang, C.-J.3    Fanwick, P.E.4    McLaughlin, J.L.5
  • 2
    • 0025886241 scopus 로고
    • Two new styryllactones, 9-deoxygoniopypyrone and 7-epigoniofufurone, from Goniothalamus giganteus
    • Fang, X.-p.; Anderson, J.E.; Chang, C.-j.; McLaughlin, J.L. Two New Styryllactones, 9-deoxygoniopypyrone and 7-Epigoniofufurone, from Goniothalamus Giganteus. J. Nat. Prod. 1991, 54, 1034-1043.
    • (1991) J. Nat. Prod. , vol.54 , pp. 1034-1043
    • Fang, X.-P.1    Anderson, J.E.2    Chang, C.-J.3    McLaughlin, J.L.4
  • 3
    • 0028656416 scopus 로고
    • Synthesis of natural and unnatural enantiomers of goniofufurone and its 7-epimers from d-glucose. Application of palladium(II)-catalyzed oxycarbonylation of unsaturated polyols
    • Gracza, T.; Jäger, V. Synthesis of Natural and Unnatural Enantiomers of Goniofufurone and Its 7-Epimers from D-Glucose. Application of Palladium(II)-Catalyzed Oxycarbonylation of Unsaturated Polyols. Synthesis 1994, 1359-1368.
    • (1994) Synthesis , pp. 1359-1368
    • Gracza, T.1    Jäger, V.2
  • 4
    • 0026325945 scopus 로고
    • 6-enitols. ω-Homologation of aldoses to produce intermediates for C-glycoside/C-nucleoside synthesis
    • 6-Enitols. ω-Homologation of Aldoses to Produce Intermediates for C-Glycoside/C-Nucleoside Synthesis. Synthesis 1991, 1108-1118.
    • (1991) Synthesis , pp. 1108-1118
    • Gracza, T.1    Hasenöhrl, T.2    Stahl, U.3    Jäger, V.4
  • 5
    • 84988086956 scopus 로고
    • Palladium(II)-catalyzed oxycarbonylation of unsaturated polyols: Synthesis of (-)-goniofufurone and assigment of absolute configuration to the natural (+)-enantiomer, a cytotoxic styryllactone
    • Gracza, T.; Jäger, V. Palladium(II)-Catalyzed Oxycarbonylation of Unsaturated Polyols: Synthesis of (-)-Goniofufurone and Assigment of Absolute Configuration to the Natural (+)-Enantiomer, a Cytotoxic Styryllactone. Synlett 1992, 191-193.
    • (1992) Synlett , pp. 191-193
    • Gracza, T.1    Jäger, V.2
  • 6
    • 0002912898 scopus 로고
    • Asymmetric synthesis. Part I. A stereoselective synthesis of benzylic centres. Derivatives of 5-C -phenyl-D-gluco-pentose and 5-C -phenyl-L-ido- pentose
    • Inch, T.D. Asymmetric Synthesis. Part I. A stereoselective synthesis of benzylic centres. Derivatives of 5-C -phenyl-D-gluco-pentose and 5-C -phenyl-L-ido-pentose. Carbohydr. Res. 1967, 5, 45-52.
    • (1967) Carbohydr. Res. , vol.5 , pp. 45-52
    • Inch, T.D.1
  • 7
    • 84988055616 scopus 로고
    • Convenient one-pot conversion of alcohols into esters via hemiacetal intermediates
    • Lichtenthaler, F.W.; Jargelis, P.; Lorenz, K. Convenient One-Pot Conversion of Alcohols into Esters via Hemiacetal Intermediates. Synthesis 1988, 790-794.
    • (1988) Synthesis , pp. 790-794
    • Lichtenthaler, F.W.1    Jargelis, P.2    Lorenz, K.3
  • 8
    • 0001517527 scopus 로고
    • The reaction of free carbonyl sugar derivatives with organometallic reagents. I. 6-Deoxy-L-idose and derivatives
    • Wolfrom, M.L.; Hanessian, S. The Reaction of Free Carbonyl Sugar Derivatives with Organometallic Reagents. I. 6-Deoxy-L-idose and Derivatives. J. Org. Chem. 1962, 27, 1800-1804.
    • (1962) J. Org. Chem. , vol.27 , pp. 1800-1804
    • Wolfrom, M.L.1    Hanessian, S.2
  • 9
    • 0027497353 scopus 로고
    • Ethoxycarbonylmethylenetriphenylphosphorane in carbohydrate chemistry, part II: A short and efficient synthesis of (+)-goniofufurone
    • Prakash, K.R.C.; Prahlada Rao, S. Ethoxycarbonylmethylenetriphenylphosphorane in Carbohydrate Chemistry, Part II: A Short and Efficient Synthesis of (+)-Goniofufurone. Tetrahedron 1993, 49, 1505-1510.
    • (1993) Tetrahedron , vol.49 , pp. 1505-1510
    • Prakash, K.R.C.1    Prahlada Rao, S.2
  • 10
    • 0001824313 scopus 로고
    • Ethoxycarbonylmethylenetriphenylphosphorane in carbohydrate chemistry, part III: A short and highly efficient synthesis of (+)-epigoniofufurone
    • Prakash, K.R.C.; Prahlada Rao, S. Ethoxycarbonylmethylenetriphenylphosphorane in Carbohydrate Chemistry, Part III: A Short and Highly Efficient Synthesis of (+)-Epigoniofufurone Synlett. 1993, 123-124.
    • (1993) Synlett , pp. 123-124
    • Prakash, K.R.C.1    Prahlada Rao, S.2
  • 12
    • 0027165778 scopus 로고
    • The total synthesis of goniofufurone
    • Murphy, P.J.; Dennison, S.T. The Total Synthesis of Goniofufurone. Tetrahedron 1993, 49, 6695-6700.
    • (1993) Tetrahedron , vol.49 , pp. 6695-6700
    • Murphy, P.J.1    Dennison, S.T.2
  • 13
    • 0004890389 scopus 로고
    • Inverted stereoselectivity in grignard additions to chiral aldehydes by use of polyethers
    • Reitstoen, B.; Kilaas, L.; Anthonsen, T. Inverted Stereoselectivity in Grignard Additions to Chiral Aldehydes by Use of Polyethers. Acta Chem. Scand., Ser. B 40 1986, 440-443.
    • (1986) Acta Chem. Scand., Ser. B 40 , pp. 440-443
    • Reitstoen, B.1    Kilaas, L.2    Anthonsen, T.3
  • 14
    • 84942812532 scopus 로고
    • Sir Geoffrey Wilkinson, F. Gordon A. Stone, Edward W. Abel, Eds.; Pergamon Press, Oxford
    • Marks, T.J.; Ernst, F.D. In Comprehensive Organometallic Chemistry; Sir Geoffrey Wilkinson, F. Gordon A. Stone, Edward W. Abel, Eds.; Pergamon Press, Oxford 1982, Volume 3, p. 173-270.
    • (1982) Comprehensive Organometallic Chemistry , vol.3 , pp. 173-270
    • Marks, T.J.1    Ernst, F.D.2
  • 15
    • 0000889671 scopus 로고
    • Organocerium reagents. Nucleophilic addition to easily enolizable ketones
    • Imamoto, T.; Sugiura, Y.; Takiyama, N. Organocerium reagents. Nucleophilic addition to easily enolizable ketones. Tetrahedron Lett. 1984, 25, 4233-4236.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 4233-4236
    • Imamoto, T.1    Sugiura, Y.2    Takiyama, N.3
  • 17
    • 0344814488 scopus 로고
    • Reaction of phenyl lithium with titanium monochloride tri-isopropoxide
    • Holloway, H. Reaction of Phenyl Lithium with Titanium Monochloride Tri-isopropoxide. Chemistry and Industry 1962, 214-215.
    • (1962) Chemistry and Industry , pp. 214-215
    • Holloway, H.1
  • 18
    • 0000730188 scopus 로고
    • Chelat- oder nicht-chelat-kontrolle bei additionsreaktionen von chiralen □- und □- alkoxycarbonyl-verbindungen
    • and references therein
    • Reetz, M.T. Chelat- oder Nicht-Chelat-Kontrolle bei Additionsreaktionen von chiralen □- und □- Alkoxycarbonyl-Verbindungen. Angew. Chem. 1984, 96, 542-555, and references therein.
    • (1984) Angew. Chem. , vol.96 , pp. 542-555
    • Reetz, M.T.1
  • 19
    • 0002291128 scopus 로고
    • Organometallverbindungen von titan und zirconium als selektive nucleophile reagentien für die organische synthese
    • Weidmann, B.; Seebach, D. Organometallverbindungen von Titan und Zirconium als selektive nucleophile Reagentien für die Organische Synthese. Angew. Chem. 1983, 95, 12-26.
    • (1983) Angew. Chem. , vol.95 , pp. 12-26
    • Weidmann, B.1    Seebach, D.2
  • 20
    • 84985520698 scopus 로고
    • Chelation- or non-chelation-control in stereoselective reactions of titanium reagents with chiral alkoxy carbonyl compounds
    • Reetz, M.T.; Kesseler, K.; Schmidtberger, S.; Wenderoth, B.; Steinbach, R. Chelation- or Non-chelation-Control in Stereoselective Reactions of Titanium Reagents with Chiral Alkoxy Carbonyl Compounds. Angew. Chem. Suppl. 1983, 1511-1526.
    • (1983) Angew. Chem. Suppl. , pp. 1511-1526
    • Reetz, M.T.1    Kesseler, K.2    Schmidtberger, S.3    Wenderoth, B.4    Steinbach, R.5
  • 21
    • 0003890189 scopus 로고
    • Reaction of 3-O-p-bromophenylsulfonyl-1,2:5,6-di-O-isopropylidene-□- D-glucofuranose with dimethylamine
    • Horton, D.; Jewell, J.S.; Prihar, H.S. Reaction of 3-O-p- bromophenylsulfonyl-1,2:5,6-di-O-isopropylidene-□-D-glucofuranose with dimethylamine. Can. J. Chem. 1968, 46, 1580-1582.
    • (1968) Can. J. Chem. , vol.46 , pp. 1580-1582
    • Horton, D.1    Jewell, J.S.2    Prihar, H.S.3
  • 22
    • 0342636970 scopus 로고
    • Ester der methansulfonsäure in der zuckergruppe
    • Helferich, B.; Dressler, H.; Griebel, R. Ester der Methansulfonsäure in der Zuckergruppe. J. Prakt. Chem. 1939, 153, 285-299.
    • (1939) J. Prakt. Chem. , vol.153 , pp. 285-299
    • Helferich, B.1    Dressler, H.2    Griebel, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.