메뉴 건너뛰기




Volumn 60, Issue 6, 2003, Pages 1351-1358

4-Hydroxycoumarin and related systems: Sitoselectivity of the Mitsunobu reaction with prenyl alcohols

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BIS(3,3 DIMETHYLALLYL) 4 (3,3 DIMETHYLALLYLOXY) 2 QUINOLIN 2 ONE; 1,3 DICARBONYL DERIVATIVE; 3 BIS(3,3 DIMETHYLALLYL)QUINOLINE 2,4 DIONE; 4 HYDROXY 2 QUINOLONE; 4 HYDROXYCOUMARIN DERIVATIVE; ALCOHOL DERIVATIVE; BUCHAPINE; CARBONYL DERIVATIVE; DIMETHYLALLYL ALCOHOL; PRENYL ALCOHOL DERIVATIVE; QUINOLINE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 0038485771     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-03-9737     Document Type: Article
Times cited : (9)

References (28)
  • 8
    • 0037155499 scopus 로고    scopus 로고
    • and references therein
    • b) C. Ahn and P. DeShong, J. Org. Chem., 2002, 67, 1754, and references therein.
    • (2002) J. Org. Chem. , vol.67 , pp. 1754
    • Ahn, C.1    DeShong, P.2
  • 14
    • 0037911020 scopus 로고    scopus 로고
    • note
    • b) Although we were able to confirm most of these results, with benzyl alcohol close to the O-benzyl derivate (61%), we isolated the C-alkylation product (23%) (unpublished data).
  • 16
    • 0034833742 scopus 로고    scopus 로고
    • 8 and from umbelliferone (7-hydroxycoumarin), with allyl and propargyl ethers (N. C. Ganguly, A. K. Sukai, S. Dutta, and P. De, J. Indian Chem. Soc., 2001, 78, 380), or cyclic ethers as exemplified by the synthesis of calanolides (S. Gaddam, A. Khilevich, C. Filer, J. D. Rizzo, J. Giltner, M. T. Flavin, and Z.-Q. Xu, J. Labelled Comp. & Radiopharm., 1997, 39, 901). Important applications to the alkylation of the phenolic hydroxyl in the coumarin core have been described in the preparation of novobiocyn derivatives (V. Jenneret, P. Vogel, P. Renaut, J. Millet, J. Theveniaux, and V. Barberousse, Bioorg. & Med. Chem. Lett., 1998, 8, 1687) and of aryl-coumarin-based inhibitors of gyrase B (S. A. Everett, E. Swann, M. A. Naylor, M. R. L. Stratford, K. B. Patel, N. Tian, R. G. Newman, B. Vojnovic, C. J. Moody, and P. Wardman, Biochem. Pharmac., 2002, 63, 1629).
    • (2001) J. Indian Chem. Soc , vol.78 , pp. 380
    • Ganguly, N.C.1    Sukai, A.K.2    Dutta, S.3    De, P.4
  • 17
    • 0030721564 scopus 로고    scopus 로고
    • 8 and from umbelliferone (7-hydroxycoumarin), with allyl and propargyl ethers (N. C. Ganguly, A. K. Sukai, S. Dutta, and P. De, J. Indian Chem. Soc., 2001, 78, 380), or cyclic ethers as exemplified by the synthesis of calanolides (S. Gaddam, A. Khilevich, C. Filer, J. D. Rizzo, J. Giltner, M. T. Flavin, and Z.-Q. Xu, J. Labelled Comp. & Radiopharm., 1997, 39, 901). Important applications to the alkylation of the phenolic hydroxyl in the coumarin core have been described in the preparation of novobiocyn derivatives (V. Jenneret, P. Vogel, P. Renaut, J. Millet, J. Theveniaux, and V. Barberousse, Bioorg. & Med. Chem. Lett., 1998, 8, 1687) and of aryl-coumarin-based inhibitors of gyrase B (S. A. Everett, E. Swann, M. A. Naylor, M. R. L. Stratford, K. B. Patel, N. Tian, R. G. Newman, B. Vojnovic, C. J. Moody, and P. Wardman, Biochem. Pharmac., 2002, 63, 1629).
    • (1997) J. Labelled Comp. & Radiopharm. , vol.39 , pp. 901
    • Gaddam, S.1    Khilevich, A.2    Filer, C.3    Rizzo, J.D.4    Giltner, J.5    Flavin, M.T.6    Xu, Z.-Q.7
  • 18
    • 0032493476 scopus 로고    scopus 로고
    • 8 and from umbelliferone (7-hydroxycoumarin), with allyl and propargyl ethers (N. C. Ganguly, A. K. Sukai, S. Dutta, and P. De, J. Indian Chem. Soc., 2001, 78, 380), or cyclic ethers as exemplified by the synthesis of calanolides (S. Gaddam, A. Khilevich, C. Filer, J. D. Rizzo, J. Giltner, M. T. Flavin, and Z.-Q. Xu, J. Labelled Comp. & Radiopharm., 1997, 39, 901). Important applications to the alkylation of the phenolic hydroxyl in the coumarin core have been described in the preparation of novobiocyn derivatives (V. Jenneret, P. Vogel, P. Renaut, J. Millet, J. Theveniaux, and V. Barberousse, Bioorg. & Med. Chem. Lett., 1998, 8, 1687) and of aryl-coumarin-based inhibitors of gyrase B (S. A. Everett, E. Swann, M. A. Naylor, M. R. L. Stratford, K. B. Patel, N. Tian, R. G. Newman, B. Vojnovic, C. J. Moody, and P. Wardman, Biochem. Pharmac., 2002, 63, 1629).
    • (1998) Bioorg. & Med. Chem. Lett. , vol.8 , pp. 1687
    • Jenneret, V.1    Vogel, P.2    Renaut, P.3    Millet, J.4    Theveniaux, J.5    Barberousse, V.6
  • 19
    • 0036569920 scopus 로고    scopus 로고
    • 8 and from umbelliferone (7-hydroxycoumarin), with allyl and propargyl ethers (N. C. Ganguly, A. K. Sukai, S. Dutta, and P. De, J. Indian Chem. Soc., 2001, 78, 380), or cyclic ethers as exemplified by the synthesis of calanolides (S. Gaddam, A. Khilevich, C. Filer, J. D. Rizzo, J. Giltner, M. T. Flavin, and Z.-Q. Xu, J. Labelled Comp. & Radiopharm., 1997, 39, 901). Important applications to the alkylation of the phenolic hydroxyl in the coumarin core have been described in the preparation of novobiocyn derivatives (V. Jenneret, P. Vogel, P. Renaut, J. Millet, J. Theveniaux, and V. Barberousse, Bioorg. & Med. Chem. Lett., 1998, 8, 1687) and of aryl-coumarin-based inhibitors of gyrase B (S. A. Everett, E. Swann, M. A. Naylor, M. R. L. Stratford, K. B. Patel, N. Tian, R. G. Newman, B. Vojnovic, C. J. Moody, and P. Wardman, Biochem. Pharmac., 2002, 63, 1629).
    • (2002) Biochem. Pharmac. , vol.63 , pp. 1629
    • Everett, S.A.1    Swann, E.2    Naylor, M.A.3    Stratford, M.R.L.4    Patel, K.B.5    Tian, N.6    Newman, R.G.7    Vojnovic, B.8    Moody, C.J.9    Wardman, P.10


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.