메뉴 건너뛰기




Volumn 69, Issue 17, 2004, Pages 5712-5719

Total syntheses of (+)- and (-)-cacospongionolide B, cacospongionolide E, and related analogues. Preliminary study of structural features acquired for phospholipase A2 inhibition

Author keywords

[No Author keywords available]

Indexed keywords

ENZYMES; METABOLITES;

EID: 4043093297     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049285e     Document Type: Article
Times cited : (61)

References (152)
  • 14
    • 0027118903 scopus 로고
    • (f) Mann, J. Nature 1992, 358, 540.
    • (1992) Nature , vol.358 , pp. 540
    • Mann, J.1
  • 22
    • 0037009967 scopus 로고    scopus 로고
    • For a preliminary report on the synthesis of cacospongionolide B, see Cheung, A. K.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 11584-11585.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 11584-11585
    • Cheung, A.K.1    Snapper, M.L.2
  • 24
    • 4043112948 scopus 로고    scopus 로고
    • and references therein. For the total synthesis of cacospongionolide F, see Darntew, D.; Forsyth, C. J. Org. Lett. 2003, 5, 991-994.
    • (2003) J. Org. Lett. , vol.5 , pp. 991-994
    • Darntew, D.1    Forsyth, C.2
  • 34
    • 0000449913 scopus 로고
    • For a review on the generating quaternary carbon centers, see Martin, S. F. Tetrahedron 1980, 36, 419-460.
    • (1980) Tetrahedron , vol.36 , pp. 419-460
    • Martin, S.F.1
  • 72
    • 0030607168 scopus 로고    scopus 로고
    • For a recent review see (h) Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853-12910.
    • (1996) Tetrahedron , vol.52 , pp. 12853-12910
    • Wipf, P.1    Jahn, H.2
  • 97
    • 33947477187 scopus 로고    scopus 로고
    • (c) Corey, E. J.; Hartmann, R.; Vatakencherry, P. A. 1962, 84, 2611-2614
    • (c) Corey, E. J.; Hartmann, R.; Vatakencherry, P. A. 1962, 84, 2611-2614.
  • 103
    • 0001292914 scopus 로고
    • Smith and Mewshaw observed no alkylation of similar lithium enolate with irans-1-iodo-3-pentene: Smith, A. B., III; Mewshaw, R. J. Org. Chem. 1984, 49, 3685-3689.
    • (1984) J. Org. Chem. , vol.49 , pp. 3685-3689
    • Smith III, A.B.1    Mewshaw, R.2
  • 110
  • 117
    • 0001091845 scopus 로고
    • For examples of related transformations, see (a) Stork, G.; Ganem, B. J. Am. Chem. Soc. 1973, 95, 6152-6153.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 6152-6153
    • Stork, G.1    Ganem, B.2
  • 121
    • 4043118517 scopus 로고    scopus 로고
    • note
    • 1H NMR (i.e., <5%).
  • 129
    • 0001631513 scopus 로고    scopus 로고
    • For recent reviews on catalytic asymmetric hydrogenation, see (a) Noyori, R. Acta Chem. Scared 1996, 50, 380-390.
    • (1996) Acta Chem. Scared , vol.50 , pp. 380-390
    • Noyori, R.1
  • 135
    • 4043072949 scopus 로고    scopus 로고
    • note
    • Higher conversions gave significant amounts of pyran-olefin reduction that can be removed at a later stage by RP-HPLC.
  • 137
    • 0002557259 scopus 로고    scopus 로고
    • For other syntheses of γ-hydroxybutenolide rings, see (a) Boukouvalas, J.; Lachance, N. Synlett 1998, 31-32.
    • (1998) Synlett , pp. 31-32
    • Boukouvalas, J.1    Lachance, N.2
  • 144
    • 4043082909 scopus 로고    scopus 로고
    • note
    • At higher conversions, lower yields of the desired compound are obtained due to reduction of the trisubstituted dihydropyran olefin.
  • 145
    • 4043149499 scopus 로고    scopus 로고
    • note
    • Contaminated with starting material and over-reduced materials.
  • 150
    • 4043071480 scopus 로고    scopus 로고
    • note
    • 2 Assay Kit from Cayman Chemical, Ann Arbor, MI (Catalog 765001).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.