메뉴 건너뛰기




Volumn 67, Issue 26, 2002, Pages 9468-9470

Synthesis of C-3′ methyl taxotere (docetaxel)

Author keywords

[No Author keywords available]

Indexed keywords

PROTECTING GROUPS;

EID: 0037184831     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026460n     Document Type: Article
Times cited : (26)

References (31)
  • 5
    • 0030283349 scopus 로고    scopus 로고
    • (e) Jenkins, P. Chem. Britain 1996, 32 (11), 43-46.
    • (1996) Chem. Britain , vol.32 , Issue.11 , pp. 43-46
    • Jenkins, P.1
  • 8
    • 37049077584 scopus 로고
    • Denis, J.-N.; Fkyerat, A.; Gimbert, Y.; Coutterez, C.; Mantellier, P.; Jost, S.; Greene, A. E. J. Chem Soc., Perkin Trans. I 1995, 1811-1815. See also: Génisson, Y.; Massardier, C.; Gautier-Luneau, I.; Greene, A. E. J. Chem Soc., Perkin Trans. 1 1996, 2869-2872. Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. Ojima, I.; Wang, T.; Delaloge, F. Tetrahedron Lett. 1998, 39, 3663-3666. Barboni, L.; Lambertucci, C.; Ballini, R.; Appendino, G.; Bombardelli, E. Tetrahedron Lett. 1998, 39, 7177-7180.
    • (1995) J. Chem Soc., Perkin Trans. I , pp. 1811-1815
    • Denis, J.-N.1    Fkyerat, A.2    Gimbert, Y.3    Coutterez, C.4    Mantellier, P.5    Jost, S.6    Greene, A.E.7
  • 9
    • 0242617763 scopus 로고    scopus 로고
    • Denis, J.-N.; Fkyerat, A.; Gimbert, Y.; Coutterez, C.; Mantellier, P.; Jost, S.; Greene, A. E. J. Chem Soc., Perkin Trans. I 1995, 1811-1815. See also: Génisson, Y.; Massardier, C.; Gautier-Luneau, I.; Greene, A. E. J. Chem Soc., Perkin Trans. 1 1996, 2869-2872. Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. Ojima, I.; Wang, T.; Delaloge, F. Tetrahedron Lett. 1998, 39, 3663-3666. Barboni, L.; Lambertucci, C.; Ballini, R.; Appendino, G.; Bombardelli, E. Tetrahedron Lett. 1998, 39, 7177-7180.
    • (1996) J. Chem Soc., Perkin Trans. 1 , pp. 2869-2872
    • Génisson, Y.1    Massardier, C.2    Gautier-Luneau, I.3    Greene, A.E.4
  • 10
    • 16044369708 scopus 로고    scopus 로고
    • Denis, J.-N.; Fkyerat, A.; Gimbert, Y.; Coutterez, C.; Mantellier, P.; Jost, S.; Greene, A. E. J. Chem Soc., Perkin Trans. I 1995, 1811-1815. See also: Génisson, Y.; Massardier, C.; Gautier-Luneau, I.; Greene, A. E. J. Chem Soc., Perkin Trans. 1 1996, 2869-2872. Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. Ojima, I.; Wang, T.; Delaloge, F. Tetrahedron Lett. 1998, 39, 3663-3666. Barboni, L.; Lambertucci, C.; Ballini, R.; Appendino, G.; Bombardelli, E. Tetrahedron Lett. 1998, 39, 7177-7180.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 6495-6498
    • Kant, J.1    Schwartz, W.S.2    Fairchild, C.3    Gao, Q.4    Huang, S.5    Long, B.H.6    Kadow, J.F.7    Farina, V.8    Vyas, D.9
  • 11
    • 0032575139 scopus 로고    scopus 로고
    • Denis, J.-N.; Fkyerat, A.; Gimbert, Y.; Coutterez, C.; Mantellier, P.; Jost, S.; Greene, A. E. J. Chem Soc., Perkin Trans. I 1995, 1811-1815. See also: Génisson, Y.; Massardier, C.; Gautier-Luneau, I.; Greene, A. E. J. Chem Soc., Perkin Trans. 1 1996, 2869-2872. Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. Ojima, I.; Wang, T.; Delaloge, F. Tetrahedron Lett. 1998, 39, 3663-3666. Barboni, L.; Lambertucci, C.; Ballini, R.; Appendino, G.; Bombardelli, E. Tetrahedron Lett. 1998, 39, 7177-7180.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3663-3666
    • Ojima, I.1    Wang, T.2    Delaloge, F.3
  • 12
    • 0032563850 scopus 로고    scopus 로고
    • Denis, J.-N.; Fkyerat, A.; Gimbert, Y.; Coutterez, C.; Mantellier, P.; Jost, S.; Greene, A. E. J. Chem Soc., Perkin Trans. I 1995, 1811-1815. See also: Génisson, Y.; Massardier, C.; Gautier-Luneau, I.; Greene, A. E. J. Chem Soc., Perkin Trans. 1 1996, 2869-2872. Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498. Ojima, I.; Wang, T.; Delaloge, F. Tetrahedron Lett. 1998, 39, 3663-3666. Barboni, L.; Lambertucci, C.; Ballini, R.; Appendino, G.; Bombardelli, E. Tetrahedron Lett. 1998, 39, 7177-7180.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7177-7180
    • Barboni, L.1    Lambertucci, C.2    Ballini, R.3    Appendino, G.4    Bombardelli, E.5
  • 13
    • 12244289216 scopus 로고    scopus 로고
    • note
    • In view of the large number of diverse taxol and taxotere derivatives published to date, it is surprising that this is apparently the first example of substitution at C-3′.
  • 17
    • 0001521888 scopus 로고
    • For general reviews on asymmetric methods to create quaternary centers and use of these methods in natural product synthesis, see: Fuji, K. Chem. Rev. 1993, 93, 2037-2066. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401 and references therein.
    • (1993) Chem. Rev. , vol.93 , pp. 2037-2066
    • Fuji, K.1
  • 18
    • 0032473509 scopus 로고    scopus 로고
    • and references therein
    • For general reviews on asymmetric methods to create quaternary centers and use of these methods in natural product synthesis, see: Fuji, K. Chem. Rev. 1993, 93, 2037-2066. Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401 and references therein.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 388-401
    • Corey, E.J.1    Guzman-Perez, A.2
  • 22
    • 12244292625 scopus 로고    scopus 로고
    • Lancaster Synthesis, Bischheim-Strasbourg, France
    • Lancaster Synthesis, Bischheim-Strasbourg, France.
  • 23
    • 12244267636 scopus 로고    scopus 로고
    • note
    • Our earlier efforts with 1-phenylethylamine and 1-(2,6-dichlorophenyl)ethylamine were unsuccessful: the β-lactam resulting from the former could not be cleanly freed of the α-methylbenzyl group and the acetophenone imine derived from the latter proved a poor ketene partner in the Staudinger reaction.
  • 25
    • 12244256715 scopus 로고    scopus 로고
    • note
    • For comparison, the imine from benzaldehyde and 1-phenylethylamine with acetoxyacetyl chloride has been reported to give diastereomeric ratios of 60:40 and 75:25 (60 and 74% yields).
  • 26
    • 0000344501 scopus 로고    scopus 로고
    • See also ref 4a,c
    • For a recent discussion of the stereochemical outcome of the Staudinger reaction, see: Arrieta, A.; Lecea, B.; Cossio, F. P. J. Org. Chem. 1998, 63, 5869-5876. See also ref 4a,c.
    • (1998) J. Org. Chem. , vol.63 , pp. 5869-5876
    • Arrieta, A.1    Lecea, B.2    Cossio, F.P.3
  • 27
    • 12244285602 scopus 로고    scopus 로고
    • note
    • In THF, the ratio was higher, but the yield was considerably lower (83:17, 43%). Solvent effects on the ratio of diastereomers in the Staudinger reaction have previous been noted. See, for example, ref 7a.
  • 28
    • 12244259651 scopus 로고    scopus 로고
    • note
    • 3, F(000) = 752, θ range 2.10-72°, 2229 measured reflections, 2229 independent reflections, R(1) [I > 1.5σ] = 0.044, wR2 [all data] = 0.0468, GoF (all data) = 1.887.
  • 29
    • 12244272363 scopus 로고    scopus 로고
    • note
    • 3, F(000) = 332, θ range 2.63-30° 10 043 measured reflections, 4544 [R(int) = 0.09] independent reflections, R(1) [I > 3σ] = 0.0496, wR2 [all data] = 0.0664, GoF (all data) = 1.903.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.