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Volumn 48, Issue 36, 2007, Pages 6397-6400

Tandem Heck-Suzuki-Miyaura reaction: Application to the synthesis of constrained analogues of combretastatin A-4

Author keywords

Combretastatin A4; Domino reaction; Oxindole; Palladium catalysis

Indexed keywords

BORONIC ACID DERIVATIVE; COMBRETASTATIN A4; OXINDOLE; PALLADIUM;

EID: 34547665222     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.129     Document Type: Article
Times cited : (40)

References (25)
  • 1
    • 33845286942 scopus 로고    scopus 로고
    • and references cited therein
    • Lippert III J.W. Bioorg. Med. Chem. 15 (2007) 605-615 and references cited therein
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 605-615
    • Lippert III, J.W.1
  • 11
    • 33750305101 scopus 로고    scopus 로고
    • An analogous tandem process was recently reported by a rhodium-catalysis. See:
    • An analogous tandem process was recently reported by a rhodium-catalysis. See:. Shintani R., Yamagami T., and Hayashi T. Org. Lett. 8 (2006) 4799-4801
    • (2006) Org. Lett. , vol.8 , pp. 4799-4801
    • Shintani, R.1    Yamagami, T.2    Hayashi, T.3
  • 14
    • 34547701729 scopus 로고    scopus 로고
    • note
    • For the desired CA4 analogues of type II, stereochemistry would be trans for the double bond Ca-Cb and cis for the exocyclic one. This corresponds to the configuration (EE) for the oxindole derivatives.
  • 15
    • 27544445308 scopus 로고    scopus 로고
    • Alkynamides 4a, 4b and 4e have already been reported, 4a and 4b being synthesized by acylation of 7a with the methyl ester of 8a or 8b. See:
    • Alkynamides 4a, 4b and 4e have already been reported, 4a and 4b being synthesized by acylation of 7a with the methyl ester of 8a or 8b. See:. Yanada R., Obika S., Kobayashi Y., Inokuma T., Oyama M., Yanada K., and Takemoto Y. Adv. Synth. Catal. 347 (2005) 1632-1642
    • (2005) Adv. Synth. Catal. , vol.347 , pp. 1632-1642
    • Yanada, R.1    Obika, S.2    Kobayashi, Y.3    Inokuma, T.4    Oyama, M.5    Yanada, K.6    Takemoto, Y.7
  • 18
    • 33750986811 scopus 로고    scopus 로고
    • Several 3-trimethoxybenzylidene oxindoles with the (E)-configuration were obtained by coupling trimethoxybenzaldehyde and the appropriate indolinone in the presence of piperidine. But these derivatives are reported to gradually isomerize to the (Z)-isomeric forms, which does not inhibit tubulin polymerization. See:
    • Several 3-trimethoxybenzylidene oxindoles with the (E)-configuration were obtained by coupling trimethoxybenzaldehyde and the appropriate indolinone in the presence of piperidine. But these derivatives are reported to gradually isomerize to the (Z)-isomeric forms, which does not inhibit tubulin polymerization. See:. Andreani A., Burnelli S., Granaiola M., Leoni A., Locatelli A., Morigi R., Rambaldi M., Varoli L., and Kunkel M.W. J. Med. Chem. 49 (2006) 6922-6924
    • (2006) J. Med. Chem. , vol.49 , pp. 6922-6924
    • Andreani, A.1    Burnelli, S.2    Granaiola, M.3    Leoni, A.4    Locatelli, A.5    Morigi, R.6    Rambaldi, M.7    Varoli, L.8    Kunkel, M.W.9
  • 22
    • 34547688769 scopus 로고    scopus 로고
    • note
    • +: 428.1862; found: 428.1852.
  • 25
    • 34547690610 scopus 로고    scopus 로고
    • note
    • For compound (EZ)-IIb, a positive NOE was observed between the methyl substituent of the exocyclic double bond and the aromatic proton in the 4-position of the indole core.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.