메뉴 건너뛰기




Volumn , Issue 15, 2007, Pages 2397-2403

Selective synthesis of ent-15-epi-F2t-isoprostane and a deuterated derivative

Author keywords

Asymmetric synthesis; Lipids; Metathesis; Olefination

Indexed keywords

ASYMMETRIC SYNTHESIS; METATHESIS; OLEFINATION;

EID: 34547805568     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983768     Document Type: Article
Times cited : (19)

References (68)
  • 1
    • 0025572704 scopus 로고    scopus 로고
    • For free radical peroxidation of arachidonic acid, see: (a) Morrow, J. D.; Hill, K. E.; Burk, R. F.; Nammour, T. M.; Badr, K. F.; Roberts, L. J. II Proc. Nat. Acad. Sci. U.S.A. 1990, 87, 9383.
    • For free radical peroxidation of arachidonic acid, see: (a) Morrow, J. D.; Hill, K. E.; Burk, R. F.; Nammour, T. M.; Badr, K. F.; Roberts, L. J. II Proc. Nat. Acad. Sci. U.S.A. 1990, 87, 9383.
  • 2
    • 0026443725 scopus 로고    scopus 로고
    • Morrow, J. D.; Awad, J. A.; Boss, H. J.; Blair, I. A.; Roberts, L. J. II Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 10721.
    • (b) Morrow, J. D.; Awad, J. A.; Boss, H. J.; Blair, I. A.; Roberts, L. J. II Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 10721.
  • 3
    • 0027968938 scopus 로고    scopus 로고
    • Morrow, J. D.; Minton, T. A.; Mukundan, C. R.; Campbell, M. D.; Zackert, W. E.; Daniel, V. C.; Badr, K. F.; Blair, I. A.; Roberts, L. J. II J. Biol. Chem. 1994, 269, 4317.
    • (c) Morrow, J. D.; Minton, T. A.; Mukundan, C. R.; Campbell, M. D.; Zackert, W. E.; Daniel, V. C.; Badr, K. F.; Blair, I. A.; Roberts, L. J. II J. Biol. Chem. 1994, 269, 4317.
  • 5
    • 0029817359 scopus 로고    scopus 로고
    • Morrow, J. D.; Awad, J. A.; Wu, A.; Zackert, W. E.; Daniel, V. C.; Roberts, L. J. II J. Biol. Chem. 1996, 271, 23185.
    • (e) Morrow, J. D.; Awad, J. A.; Wu, A.; Zackert, W. E.; Daniel, V. C.; Roberts, L. J. II J. Biol. Chem. 1996, 271, 23185.
  • 40
    • 0000051768 scopus 로고
    • For earlier studies on ring-opening cross-metathesis of cyclobutenes, see: b
    • For earlier studies on ring-opening cross-metathesis of cyclobutenes, see: (b) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610.
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 9610
    • Randall, M.L.1    Tallarico, J.A.2    Snapper, M.L.3
  • 44
    • 34547733462 scopus 로고    scopus 로고
    • Ph.D. Thesis; Boston College: Chestnut Hill Massachusetts
    • Schrader, T. O. Ph.D. Thesis; Boston College: Chestnut Hill Massachusetts, 2002.
    • (2002)
    • Schrader, T.O.1
  • 47
    • 33748413162 scopus 로고    scopus 로고
    • For a more recent and convenient approach to this intermediate, see
    • For a more recent and convenient approach to this intermediate, see: Zhao, Y.; Rodrigo, J.; Hoveyda, A. H.; Snapper, M. L. Nature (London) 2006, 443, 67.
    • (2006) Nature (London) , vol.443 , pp. 67
    • Zhao, Y.1    Rodrigo, J.2    Hoveyda, A.H.3    Snapper, M.L.4
  • 52
    • 34547806630 scopus 로고    scopus 로고
    • Regioselectivity was determined by COSY NMR
    • Regioselectivity was determined by COSY NMR.
  • 54
    • 34547759267 scopus 로고    scopus 로고
    • 1H NMR (estimated detection limits of 20:1) by comparison with authentic samples of each diastereomer.
    • 1H NMR (estimated detection limits of 20:1) by comparison with authentic samples of each diastereomer.
  • 56
    • 14644401026 scopus 로고    scopus 로고
    • This isotopically labeled isoprostane could be used as an alternative standard for metabolic studies as shown in: Kim, S, Powell, W. S, Lawson, J. A, Jacobo, S. H, Pratico, D, FitzGerald, G. A, Maxey, K, Rokach, J. Bioorg. Med. Chem. Lett. 2005, 15, 1613
    • This isotopically labeled isoprostane could be used as an alternative standard for metabolic studies as shown in: Kim, S.; Powell, W. S.; Lawson, J. A.; Jacobo, S. H.; Pratico, D.; FitzGerald, G. A.; Maxey, K.; Rokach, J. Bioorg. Med. Chem. Lett. 2005, 15, 1613.
  • 58
    • 34547816628 scopus 로고    scopus 로고
    • For selected examples of GC/MS studies for the analysis of isoprostanes, see: (a) Roberts, L. J. II; Morrow, J. D. In Methods in Biological Oxidative Stress; Hensley, K.; Floyd, R. A., Eds.; Humana Press: Totawa NJ, 2003, Chap. 4, 33-39.
    • For selected examples of GC/MS studies for the analysis of isoprostanes, see: (a) Roberts, L. J. II; Morrow, J. D. In Methods in Biological Oxidative Stress; Hensley, K.; Floyd, R. A., Eds.; Humana Press: Totawa NJ, 2003, Chap. 4, 33-39.
  • 59
    • 0025058849 scopus 로고    scopus 로고
    • Morrow, J. D.; Harris, T. M.; Roberts, L. J. II Anal. Biochem. 1990, 184, 1.
    • (b) Morrow, J. D.; Harris, T. M.; Roberts, L. J. II Anal. Biochem. 1990, 184, 1.
  • 64
    • 34547777389 scopus 로고    scopus 로고
    • More details on the setup and results of the GC/MS detection assay may be obtained by contacting the authors
    • More details on the setup and results of the GC/MS detection assay may be obtained by contacting the authors.
  • 67
    • 34547754516 scopus 로고    scopus 로고
    • Data shown for a 74% yield reaction. Yields range from 70-90%, depending on catalyst purity.
    • Data shown for a 74% yield reaction. Yields range from 70-90%, depending on catalyst purity.
  • 68
    • 34547821448 scopus 로고    scopus 로고
    • This compound is the major isomer; however, it is in a mixture of isomers of lower deuterium incorporation
    • This compound is the major isomer; however, it is in a mixture of isomers of lower deuterium incorporation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.