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Volumn 11, Issue 16, 2009, Pages 3602-3605

Total synthesis and bioactivity of resolvin E2

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFLAMMATORY AGENT; CYTOKINE; DRUG DERIVATIVE; ICOSAPENTAENOIC ACID; RESOLVIN E2; ZYMOSAN;

EID: 68949122370     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901350g     Document Type: Article
Times cited : (75)

References (38)
  • 6
    • 7244242688 scopus 로고    scopus 로고
    • Total syntheses of resolvins E1 were disclosed in ref 2a. Total synthesis of resolvins D2 and D5 were reported. (a) Rodriguez, A. R.; Spur, B. W. Tetrahedron Lett. 2004, 45, 8717-8720.
    • Total syntheses of resolvins E1 were disclosed in ref 2a. Total synthesis of resolvins D2 and D5 were reported. (a) Rodriguez, A. R.; Spur, B. W. Tetrahedron Lett. 2004, 45, 8717-8720.
  • 9
    • 0001414464 scopus 로고
    • For rationalization of torquoselectivity, see: a
    • For rationalization of torquoselectivity, see: (a) Rudolf, K.; Spell-meyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 3708-3710.
    • (1987) J. Org. Chem , vol.52 , pp. 3708-3710
    • Rudolf, K.1    Spell-meyer, D.C.2    Houk, K.N.3
  • 12
    • 0026565383 scopus 로고    scopus 로고
    • Wallace demonstrated selective ring opening of cyclobutene aldehydes and substrate-controlled stereoselective introductions of various carbon nucleophiles to disubstituted cyclobutenes: (a) Binns, F, Hayes, R, Ingham, S, Saengchantara, S. T, Turner, R. W, Wallace, T. W. Tetrahedron 1992, 48, 515-530
    • Wallace demonstrated selective ring opening of cyclobutene aldehydes and substrate-controlled stereoselective introductions of various carbon nucleophiles to disubstituted cyclobutenes: (a) Binns, F.; Hayes, R.; Ingham, S.; Saengchantara, S. T.; Turner, R. W.; Wallace, T. W. Tetrahedron 1992, 48, 515-530.
  • 16
    • 0033548151 scopus 로고    scopus 로고
    • Enantioselective syntheses of (+)- and (-)-6 by enzymatic resolution were reported: Gourdel-Martin, M.-E.; Comoy, C.; Huet, F. Tetrahedron: Asymmetry 1999, 10, 403-404. See also ref 6b and 6c.
    • Enantioselective syntheses of (+)- and (-)-6 by enzymatic resolution were reported: Gourdel-Martin, M.-E.; Comoy, C.; Huet, F. Tetrahedron: Asymmetry 1999, 10, 403-404. See also ref 6b and 6c.
  • 20
    • 33845420420 scopus 로고    scopus 로고
    • For a review of synthetic applications of lactone 6 and derivatives, see: Gauvry, N.; Lescop, C.; Huet, F. Eur. J. Org. Chem. 2006, 520, 7-5218.
    • For a review of synthetic applications of lactone 6 and derivatives, see: Gauvry, N.; Lescop, C.; Huet, F. Eur. J. Org. Chem. 2006, 520, 7-5218.
  • 22
    • 0041378031 scopus 로고    scopus 로고
    • For a review of asymmetric alcoholysis of cyclic anhydrides, see
    • For a review of asymmetric alcoholysis of cyclic anhydrides, see: Chen, Y.; McDaid, P.; Deng, L. Chem. Rev. 2003, 103, 2965-2983.
    • (2003) Chem. Rev , vol.103 , pp. 2965-2983
    • Chen, Y.1    McDaid, P.2    Deng, L.3
  • 23
    • 68949114873 scopus 로고    scopus 로고
    • 1H NMR spectra of the MTPA ester of alcohol 11.
    • 1H NMR spectra of the MTPA ester of alcohol 11.
  • 24
    • 68949136057 scopus 로고    scopus 로고
    • Absolute configuration of lactone 6 was deduced from the report of Wallace and co-workers, see ref 6d
    • Absolute configuration of lactone 6 was deduced from the report of Wallace and co-workers, see ref 6d.
  • 28
    • 2142858450 scopus 로고    scopus 로고
    • Stereochemistries at C5 and C18 positions were unambiguously determined by the modified Moshers' method. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096. See Supporting Information for the detailed procedure.
    • Stereochemistries at C5 and C18 positions were unambiguously determined by the modified Moshers' method. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096. See Supporting Information for the detailed procedure.
  • 29
    • 68949149562 scopus 로고    scopus 로고
    • E,Z-Dienes 20 and 24 were easily isomerized into E,E-diene upon standing at room temperature. Thus, organic solution of the reaction mixture from the oxidation was directly used for the reduction
    • E,Z-Dienes 20 and 24 were easily isomerized into E,E-diene upon standing at room temperature. Thus, organic solution of the reaction mixture from the oxidation was directly used for the reduction.
  • 32
    • 68949131546 scopus 로고    scopus 로고
    • 3P gave only trace amount of the product 2.
    • 3P gave only trace amount of the product 2.
  • 33
    • 68949085834 scopus 로고    scopus 로고
    • 3Et gave the desired product as a single isomer; however, the yield was 23%.
    • 3Et gave the desired product as a single isomer; however, the yield was 23%.


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