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Volumn 9, Issue 22, 2007, Pages 4619-4622

Total synthesis of iejimalide B. An application of the Shiina macrolactonization

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CARBAMIC ACID DERIVATIVE; IEJIMALIDE B; MACROLIDE; UNCLASSIFIED DRUG;

EID: 35948932526     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702129w     Document Type: Article
Times cited : (31)

References (48)
  • 6
    • 35949001362 scopus 로고    scopus 로고
    • National Cancer Institute Developmental Therapeutics Program, NSC: 727699, Test Date: July 21, 2003, http://www.dtp.nci.nih.gov/docs/dtp_search. html.
    • National Cancer Institute Developmental Therapeutics Program, NSC: 727699, Test Date: July 21, 2003, http://www.dtp.nci.nih.gov/docs/dtp_search. html.
  • 9
    • 35949000586 scopus 로고    scopus 로고
    • McHenry, P.; Wang, W. L.; Jeffrey, R.; Devitt, E.; Kluesner, N.; Schweitzer, D.; Helquist, P.; Tenniswood, M. Iejimalide A and Iejimalide B Induce S-phase Arrest or Apoptosis Through a Potentially p53-independent Pathway (Poster 791.7), Experimental Biology, Washington, DC, April 28-May 2, 2007.
    • (b) McHenry, P.; Wang, W. L.; Jeffrey, R.; Devitt, E.; Kluesner, N.; Schweitzer, D.; Helquist, P.; Tenniswood, M. Iejimalide A and Iejimalide B Induce S-phase Arrest or Apoptosis Through a Potentially p53-independent Pathway (Poster 791.7), Experimental Biology, Washington, DC, April 28-May 2, 2007.
  • 13
    • 35949003294 scopus 로고    scopus 로고
    • Ph.D. Dissertation, University of Notre Dame, Notre Dame, IN
    • Kane, J. J. Ph.D. Dissertation, University of Notre Dame, Notre Dame, IN, 2003.
    • (2003)
    • Kane, J.J.1
  • 29
    • 35948966911 scopus 로고    scopus 로고
    • An inspection of the NMR spectrum of the reaction mixture taken prior to workup indicates the presence of about 65% desired product and no remaining aldehyde starting material
    • An inspection of the NMR spectrum of the reaction mixture taken prior to workup indicates the presence of about 65% desired product and no remaining aldehyde starting material.
  • 36
    • 35948994233 scopus 로고    scopus 로고
    • A similar reaction was employed by Fürstner in ref 11.
    • A similar reaction was employed by Fürstner in ref 11.
  • 39
    • 35948995865 scopus 로고    scopus 로고
    • Conditions screened: PdCl2(MeCN)2, PdCl 2(BnCN)2, PdCl2(PPh3)2, PdCl2(AsPh3)2, Pd(PPh3)4, Pd2(dba)3, CuTC, CuCl, CuI, AsPh3, P(o-Tol)3, n-Bu)4N][Ph2PO 2, LiCl, CsF, O=PPh3, BHT, and/or i-Pr 2NEt in various solvents
    • 2NEt in various solvents.
  • 45
    • 35948946213 scopus 로고    scopus 로고
    • In our hands, application of Mukaiyama conditions did not result in macrolactonization. However, the Yamaguchi macrolactonization also provided the desired product, but only in about half the yield of the Shiina method. We did not observe aromatization to a phenol during the Yamaguchi macrolactonization as was reported by Fürstner in ref 11a
    • In our hands, application of Mukaiyama conditions did not result in macrolactonization. However, the Yamaguchi macrolactonization also provided the desired product, but only in about half the yield of the Shiina method. We did not observe aromatization to a phenol during the Yamaguchi macrolactonization as was reported by Fürstner in ref 11a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.