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Volumn 9, Issue 7, 2007, Pages 1267-1270

Asymmetric total synthesis and formal total synthesis of the antitumor sesquiterpenoid (+)-eremantholide A

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; EREMANTHOLIDE A; SESQUITERPENE; UNCLASSIFIED DRUG;

EID: 34147190045     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0700862     Document Type: Article
Times cited : (87)

References (24)
  • 1
    • 0016850344 scopus 로고    scopus 로고
    • (+)-Eremantholide A isolation, structure determination, and initial antitumor evaluation: (a) Raffauf, R. F.; Huang, P.-K. C.; Le Quesne, P. W.; Levery, S. B.; Brennan, T. F. J. Am. Chem. Soc. 1975, 97, 6884.
    • (+)-Eremantholide A isolation, structure determination, and initial antitumor evaluation: (a) Raffauf, R. F.; Huang, P.-K. C.; Le Quesne, P. W.; Levery, S. B.; Brennan, T. F. J. Am. Chem. Soc. 1975, 97, 6884.
  • 3
    • 84889398397 scopus 로고    scopus 로고
    • For past total syntheses of (+)-eremantholide A, see: (a) Boeckman, R. K., Jr.; Yoon, S. K.; Heckendorn, D. K. J. Am. Chem. Soc. 1991, 113, 9682.
    • For past total syntheses of (+)-eremantholide A, see: (a) Boeckman, R. K., Jr.; Yoon, S. K.; Heckendorn, D. K. J. Am. Chem. Soc. 1991, 113, 9682.
  • 6
    • 0038809627 scopus 로고    scopus 로고
    • Although 15-acetoxy-eremantholide B inhibits NF-κB at 5 μM in Jurkat T cells, -eremantholide A does not inhibit this target at the concentrations needed to inhibit cancer cell growth. See: Rüngeler, P, Castro, V, Mora, G, Gören, N, Vichnewski, W, Pahl, H. L, Merfort, I, Schmidt, T. J. Bioorg. Med. Chem. 1999, 7, 2343
    • Although 15-acetoxy-eremantholide B inhibits NF-κB at 5 μM in Jurkat T cells, (+)-eremantholide A does not inhibit this target at the concentrations needed to inhibit cancer cell growth. See: Rüngeler, P.; Castro, V.; Mora, G.; Gören, N.; Vichnewski, W.; Pahl, H. L.; Merfort, I.; Schmidt, T. J. Bioorg. Med. Chem. 1999, 7, 2343.
  • 21
    • 34147167098 scopus 로고    scopus 로고
    • Important Note: Under these conditions, we find that 27 is always formed alongside approximately 14-17% of a lactone migration product that is difficult to remove at this stage; the latter impurity arises from attack of the C(8)-OH in 27 on its own lactone carbonyl.
    • Important Note: Under these conditions, we find that 27 is always formed alongside approximately 14-17% of a lactone migration product that is difficult to remove at this stage; the latter impurity arises from attack of the C(8)-OH in 27 on its own lactone carbonyl.
  • 24
    • 11444258937 scopus 로고    scopus 로고
    • For the successful use of 36 to construct ' the highly strained ring system of ingenol, see: Nickel, A.; Maruyama, T.; Tang, H.; Murphy, P. D.; Greene, B.; Yusuff, N.; Wood, J. L. J. Am. Chem. Soc. 2004, 126, 16300.
    • (c) For the successful use of 36 to construct ' the highly strained ring system of ingenol, see: Nickel, A.; Maruyama, T.; Tang, H.; Murphy, P. D.; Greene, B.; Yusuff, N.; Wood, J. L. J. Am. Chem. Soc. 2004, 126, 16300.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.