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Volumn 64, Issue 34, 2008, Pages 7920-7928

Synthesis of 12-aza analogs of epothilones and (E)-9,10-dehydroepothilones

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKADIENE; CARBOXYLIC ACID; EPOTHILONE DERIVATIVE; KETONE; MACROCYCLIC COMPOUND; N BOC 12 AZA EPOTHILONE;

EID: 46649099836     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.06.017     Document Type: Article
Times cited : (6)

References (55)
  • 2
    • 85055223076 scopus 로고    scopus 로고
    • Cragg G.M., Kingston D.G.I., and Newman D.J. (Eds), CRC, Boca Raton, FL
    • In: Cragg G.M., Kingston D.G.I., and Newman D.J. (Eds). Anticancer Agents from Natural Products (2005), CRC, Boca Raton, FL
    • (2005) Anticancer Agents from Natural Products
  • 4
    • 46649101171 scopus 로고    scopus 로고
    • Selected reviews:
    • Selected reviews:
  • 7
    • 10444243268 scopus 로고    scopus 로고
    • For an example where total synthesis has served to provide material of a complex natural product (discodermolide) for Phase I clinical studies see:
    • For an example where total synthesis has served to provide material of a complex natural product (discodermolide) for Phase I clinical studies see:. Mickel S.J. Curr. Opin. Drug Discov. Dev. 7 (2004) 869-881
    • (2004) Curr. Opin. Drug Discov. Dev. , vol.7 , pp. 869-881
    • Mickel, S.J.1
  • 8
    • 33947717002 scopus 로고    scopus 로고
    • For examples from the area of microtubule-stabilizing natural products see:
    • For examples from the area of microtubule-stabilizing natural products see:. Altmann K.-H., and Gertsch J. Nat. Prod. Rep. 24 (2007) 327-357
    • (2007) Nat. Prod. Rep. , vol.24 , pp. 327-357
    • Altmann, K.-H.1    Gertsch, J.2
  • 15
    • 46649109195 scopus 로고    scopus 로고
    • For recent reviews on the chemistry, biology, and clinical applications of epothilones see:
    • For recent reviews on the chemistry, biology, and clinical applications of epothilones see:
  • 17
    • 84937419962 scopus 로고    scopus 로고
    • Cragg G.M., Kingston D.G.I., and Newman D.J. (Eds), CRC, Boca Raton, FL
    • Höfle G., and Reichenbach H. In: Cragg G.M., Kingston D.G.I., and Newman D.J. (Eds). Anticancer Agents from Natural Products (2005), CRC, Boca Raton, FL 413-450
    • (2005) Anticancer Agents from Natural Products , pp. 413-450
    • Höfle, G.1    Reichenbach, H.2
  • 24
    • 46649101386 scopus 로고    scopus 로고
    • note
    • For a side-chain-modified analog of 1 with enhanced antiproliferative activity cf. Ref. 8b.
  • 25
    • 34248525107 scopus 로고    scopus 로고
    • A preliminary account of this work has appeared as a short conference report:
    • A preliminary account of this work has appeared as a short conference report:. Feyen F., Gertsch J., Wartmann M., and Altmann K.-H. Chimia 61 (2007) 143-146
    • (2007) Chimia , vol.61 , pp. 143-146
    • Feyen, F.1    Gertsch, J.2    Wartmann, M.3    Altmann, K.-H.4
  • 41
    • 46649104142 scopus 로고    scopus 로고
    • note
    • 13C data reported for 12 by Sinha and co-workers and those reported in this paper. The Supplementary data to Ref. 26 lists 22 carbon signals for 12, which does correspond to the total number of non-equivalent C-atoms. At the same time, however, the signal for the carboxylate carbon is missing from the list.Danishefsky and co-workers have described the synthesis of carboxylic acid 12a, but following a strategy different from the one discussed in this paper (Refs. 12b,d): {A figure is presented}
  • 42
    • 46649100759 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis cf., e.g.:
    • For recent reviews on olefin metathesis cf., e.g.:
  • 47
    • 46649105751 scopus 로고    scopus 로고
    • note
    • This problem was eventually overcome by the (uncomplicated and still E-selective) RCM of dienes 24a/b and introduction of the side chain subsequent to macrocyclization: {A figure is presented}


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