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Volumn 63, Issue 25, 1998, Pages 9580-9583

A formal total synthesis of epothilone A: Enantioselective preparation of the C1-C6 and C7-C12 fragments

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; EPOTHILONE A; KETONE;

EID: 0032509248     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981461u     Document Type: Article
Times cited : (38)

References (36)
  • 8
    • 0032541259 scopus 로고    scopus 로고
    • For an excellent review of the biology and chemistry of epothilones (up to February 28, 1998), see: Nicolaou, K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. Engl. 1998, 35, 2014-2045. Some more recent relevant papers include: (a) Schinzer, D.; Bauer, A.; Schieber, J. Synlett 1998, 861-864. (b) May, S. A.; Grieco, P. A. J. Chem. Soc., Chem. Commun. 1998, 1597-1598.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2014-2045
    • Nicolaou, K.C.1    Roschangar, F.2    Vourloumis, D.3
  • 9
    • 0001335104 scopus 로고    scopus 로고
    • For an excellent review of the biology and chemistry of epothilones (up to February 28, 1998), see: Nicolaou, K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. Engl. 1998, 35, 2014-2045. Some more recent relevant papers include: (a) Schinzer, D.; Bauer, A.; Schieber, J. Synlett 1998, 861-864. (b) May, S. A.; Grieco, P. A. J. Chem. Soc., Chem. Commun. 1998, 1597-1598.
    • (1998) Synlett , pp. 861-864
    • Schinzer, D.1    Bauer, A.2    Schieber, J.3
  • 10
    • 0032493824 scopus 로고    scopus 로고
    • For an excellent review of the biology and chemistry of epothilones (up to February 28, 1998), see: Nicolaou, K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. Engl. 1998, 35, 2014-2045. Some more recent relevant papers include: (a) Schinzer, D.; Bauer, A.; Schieber, J. Synlett 1998, 861-864. (b) May, S. A.; Grieco, P. A. J. Chem. Soc., Chem. Commun. 1998, 1597-1598.
    • (1998) J. Chem. Soc., Chem. Commun. , pp. 1597-1598
    • May, S.A.1    Grieco, P.A.2
  • 23
    • 0030590984 scopus 로고    scopus 로고
    • For other synthetic efforts to epothilone, see: (a) Mulzer, J.; Mantoulidis, A. Tetrahedron Lett. 1996, 37, 9179-9182. (b) Claus, E.; Pahl, A.; Jones, P. G.; Meyer, H. H.; Kalesse, M. Tetrahedron Lett. 1997, 38, 1359-1362. (c) De Brabender, J.; Rosset, S.; Bernardinelli, G. Synlett 1997, 824. (d) Mulzer, J.; Mantoulidis, A. Öhler, E. Tetrahedron Lett. 1997, 38, 7725-7728. (e) Chakraborty, T. K.; Dutta, S. Tetrahedron Lett. 1998, 39, 101-104. (f) Bijoy, P.; Avery, M. A. Tetrahedron Lett. 1998, 39, 209-212. (g) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 39, 1363-1366. (h) Liu, Z.-Y.; Yu, C.-Y.; Yang, J.-D. Synlett 1997, 1383-1384. (i) Liu, Z.-Y.; Yu, C.-Y.; Wang, R.-F.; Li, G. Tetrahedron Lett. 1998, 39, 5261-5264.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 9179-9182
    • Mulzer, J.1    Mantoulidis, A.2
  • 24
    • 0031584881 scopus 로고    scopus 로고
    • For other synthetic efforts to epothilone, see: (a) Mulzer, J.; Mantoulidis, A. Tetrahedron Lett. 1996, 37, 9179-9182. (b) Claus, E.; Pahl, A.; Jones, P. G.; Meyer, H. H.; Kalesse, M. Tetrahedron Lett. 1997, 38, 1359-1362. (c) De Brabender, J.; Rosset, S.; Bernardinelli, G. Synlett 1997, 824. (d) Mulzer, J.; Mantoulidis, A. Öhler, E. Tetrahedron Lett. 1997, 38, 7725-7728. (e) Chakraborty, T. K.; Dutta, S. Tetrahedron Lett. 1998, 39, 101-104. (f) Bijoy, P.; Avery, M. A. Tetrahedron Lett. 1998, 39, 209-212. (g) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 39, 1363-1366. (h) Liu, Z.-Y.; Yu, C.-Y.; Yang, J.-D. Synlett 1997, 1383-1384. (i) Liu, Z.-Y.; Yu, C.-Y.; Wang, R.-F.; Li, G. Tetrahedron Lett. 1998, 39, 5261-5264.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1359-1362
    • Claus, E.1    Pahl, A.2    Jones, P.G.3    Meyer, H.H.4    Kalesse, M.5
  • 25
    • 0001149958 scopus 로고    scopus 로고
    • For other synthetic efforts to epothilone, see: (a) Mulzer, J.; Mantoulidis, A. Tetrahedron Lett. 1996, 37, 9179-9182. (b) Claus, E.; Pahl, A.; Jones, P. G.; Meyer, H. H.; Kalesse, M. Tetrahedron Lett. 1997, 38, 1359-1362. (c) De Brabender, J.; Rosset, S.; Bernardinelli, G. Synlett 1997, 824. (d) Mulzer, J.; Mantoulidis, A. Öhler, E. Tetrahedron Lett. 1997, 38, 7725-7728. (e) Chakraborty, T. K.; Dutta, S. Tetrahedron Lett. 1998, 39, 101-104. (f) Bijoy, P.; Avery, M. A. Tetrahedron Lett. 1998, 39, 209-212. (g) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 39, 1363-1366. (h) Liu, Z.-Y.; Yu, C.-Y.; Yang, J.-D. Synlett 1997, 1383-1384. (i) Liu, Z.-Y.; Yu, C.-Y.; Wang, R.-F.; Li, G. Tetrahedron Lett. 1998, 39, 5261-5264.
    • (1997) Synlett , pp. 824
    • De Brabender, J.1    Rosset, S.2    Bernardinelli, G.3
  • 26
    • 0030666278 scopus 로고    scopus 로고
    • For other synthetic efforts to epothilone, see: (a) Mulzer, J.; Mantoulidis, A. Tetrahedron Lett. 1996, 37, 9179-9182. (b) Claus, E.; Pahl, A.; Jones, P. G.; Meyer, H. H.; Kalesse, M. Tetrahedron Lett. 1997, 38, 1359-1362. (c) De Brabender, J.; Rosset, S.; Bernardinelli, G. Synlett 1997, 824. (d) Mulzer, J.; Mantoulidis, A. Öhler, E. Tetrahedron Lett. 1997, 38, 7725-7728. (e) Chakraborty, T. K.; Dutta, S. Tetrahedron Lett. 1998, 39, 101-104. (f) Bijoy, P.; Avery, M. A. Tetrahedron Lett. 1998, 39, 209-212. (g) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 39, 1363-1366. (h) Liu, Z.-Y.; Yu, C.-Y.; Yang, J.-D. Synlett 1997, 1383-1384. (i) Liu, Z.-Y.; Yu, C.-Y.; Wang, R.-F.; Li, G. Tetrahedron Lett. 1998, 39, 5261-5264.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7725-7728
    • Mulzer, J.1    Mantoulidis, A.2    Öhler, E.3
  • 27
    • 0031983809 scopus 로고    scopus 로고
    • For other synthetic efforts to epothilone, see: (a) Mulzer, J.; Mantoulidis, A. Tetrahedron Lett. 1996, 37, 9179-9182. (b) Claus, E.; Pahl, A.; Jones, P. G.; Meyer, H. H.; Kalesse, M. Tetrahedron Lett. 1997, 38, 1359-1362. (c) De Brabender, J.; Rosset, S.; Bernardinelli, G. Synlett 1997, 824. (d) Mulzer, J.; Mantoulidis, A. Öhler, E. Tetrahedron Lett. 1997, 38, 7725-7728. (e) Chakraborty, T. K.; Dutta, S. Tetrahedron Lett. 1998, 39, 101-104. (f) Bijoy, P.; Avery, M. A. Tetrahedron Lett. 1998, 39, 209-212. (g) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 39, 1363-1366. (h) Liu, Z.-Y.; Yu, C.-Y.; Yang, J.-D. Synlett 1997, 1383-1384. (i) Liu, Z.-Y.; Yu, C.-Y.; Wang, R.-F.; Li, G. Tetrahedron Lett. 1998, 39, 5261-5264.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 101-104
    • Chakraborty, T.K.1    Dutta, S.2
  • 28
    • 0032518648 scopus 로고    scopus 로고
    • For other synthetic efforts to epothilone, see: (a) Mulzer, J.; Mantoulidis, A. Tetrahedron Lett. 1996, 37, 9179-9182. (b) Claus, E.; Pahl, A.; Jones, P. G.; Meyer, H. H.; Kalesse, M. Tetrahedron Lett. 1997, 38, 1359-1362. (c) De Brabender, J.; Rosset, S.; Bernardinelli, G. Synlett 1997, 824. (d) Mulzer, J.; Mantoulidis, A. Öhler, E. Tetrahedron Lett. 1997, 38, 7725-7728. (e) Chakraborty, T. K.; Dutta, S. Tetrahedron Lett. 1998, 39, 101-104. (f) Bijoy, P.; Avery, M. A. Tetrahedron Lett. 1998, 39, 209-212. (g) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 39, 1363-1366. (h) Liu, Z.-Y.; Yu, C.-Y.; Yang, J.-D. Synlett 1997, 1383-1384. (i) Liu, Z.-Y.; Yu, C.-Y.; Wang, R.-F.; Li, G. Tetrahedron Lett. 1998, 39, 5261-5264.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 209-212
    • Bijoy, P.1    Avery, M.A.2
  • 29
    • 0031584942 scopus 로고    scopus 로고
    • For other synthetic efforts to epothilone, see: (a) Mulzer, J.; Mantoulidis, A. Tetrahedron Lett. 1996, 37, 9179-9182. (b) Claus, E.; Pahl, A.; Jones, P. G.; Meyer, H. H.; Kalesse, M. Tetrahedron Lett. 1997, 38, 1359-1362. (c) De Brabender, J.; Rosset, S.; Bernardinelli, G. Synlett 1997, 824. (d) Mulzer, J.; Mantoulidis, A. Öhler, E. Tetrahedron Lett. 1997, 38, 7725-7728. (e) Chakraborty, T. K.; Dutta, S. Tetrahedron Lett. 1998, 39, 101-104. (f) Bijoy, P.; Avery, M. A. Tetrahedron Lett. 1998, 39, 209-212. (g) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 39, 1363-1366. (h) Liu, Z.-Y.; Yu, C.-Y.; Yang, J.-D. Synlett 1997, 1383-1384. (i) Liu, Z.-Y.; Yu, C.-Y.; Wang, R.-F.; Li, G. Tetrahedron Lett. 1998, 39, 5261-5264.
    • (1997) Tetrahedron Lett. , vol.39 , pp. 1363-1366
    • Gabriel, T.1    Wessjohann, L.2
  • 30
    • 0344468142 scopus 로고    scopus 로고
    • For other synthetic efforts to epothilone, see: (a) Mulzer, J.; Mantoulidis, A. Tetrahedron Lett. 1996, 37, 9179-9182. (b) Claus, E.; Pahl, A.; Jones, P. G.; Meyer, H. H.; Kalesse, M. Tetrahedron Lett. 1997, 38, 1359-1362. (c) De Brabender, J.; Rosset, S.; Bernardinelli, G. Synlett 1997, 824. (d) Mulzer, J.; Mantoulidis, A. Öhler, E. Tetrahedron Lett. 1997, 38, 7725-7728. (e) Chakraborty, T. K.; Dutta, S. Tetrahedron Lett. 1998, 39, 101-104. (f) Bijoy, P.; Avery, M. A. Tetrahedron Lett. 1998, 39, 209-212. (g) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 39, 1363-1366. (h) Liu, Z.-Y.; Yu, C.-Y.; Yang, J.-D. Synlett 1997, 1383-1384. (i) Liu, Z.-Y.; Yu, C.-Y.; Wang, R.-F.; Li, G. Tetrahedron Lett. 1998, 39, 5261-5264.
    • (1997) Synlett , pp. 1383-1384
    • Liu, Z.-Y.1    Yu, C.-Y.2    Yang, J.-D.3
  • 31
    • 0032537693 scopus 로고    scopus 로고
    • For other synthetic efforts to epothilone, see: (a) Mulzer, J.; Mantoulidis, A. Tetrahedron Lett. 1996, 37, 9179-9182. (b) Claus, E.; Pahl, A.; Jones, P. G.; Meyer, H. H.; Kalesse, M. Tetrahedron Lett. 1997, 38, 1359-1362. (c) De Brabender, J.; Rosset, S.; Bernardinelli, G. Synlett 1997, 824. (d) Mulzer, J.; Mantoulidis, A. Öhler, E. Tetrahedron Lett. 1997, 38, 7725-7728. (e) Chakraborty, T. K.; Dutta, S. Tetrahedron Lett. 1998, 39, 101-104. (f) Bijoy, P.; Avery, M. A. Tetrahedron Lett. 1998, 39, 209-212. (g) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 39, 1363-1366. (h) Liu, Z.-Y.; Yu, C.-Y.; Yang, J.-D. Synlett 1997, 1383-1384. (i) Liu, Z.-Y.; Yu, C.-Y.; Wang, R.-F.; Li, G. Tetrahedron Lett. 1998, 39, 5261-5264.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 5261-5264
    • Liu, Z.-Y.1    Yu, C.-Y.2    Wang, R.-F.3    Li, G.4
  • 34
    • 20644472574 scopus 로고    scopus 로고
    • Altus Biologics Inc., Cambridge, MA
    • Altus Biologics Inc., Cambridge, MA.


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