12,13-Isobaccatin III. Taxane enol esters (12,13-isotaxanes)

Journal of the American Chemical Society

Volumn 118, Issue 4, 1996, Pages 919-920

  Kelly, Robert C ^a   Wicnienski, Nancy A ^a   Gebhard, Ilse ^a   Qualls, Samuel J ^a   Han, Fusen ^a   Dobrowolski, Paul J ^a   Nidy, Eldon G ^a   Johnson, Roy A ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

10 ACETYLTAXOTERE; DOCETAXEL; TAXANE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; LEUKEMIA CELL; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

EID: 0030061588     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953702a     Document Type: Article

References (34)

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11. 13-Ketobaccatin III was first described in ref 1
12. Zinc reductions of 13-ketobaccatins, including 10-deacetyl-13-ketobaccatin III, under various conditions have been reported; Marder, R.; Dubois, J.; Guénard, D.. Guéritte-Voegelein, F., Potier, P Tetrahedron 1995, 51, 1985.
13. 10-Deacetyl-11,12-dihydrobaccatin III-7-O-TES is described in ref 9, as well as in the following: Appendino, G.; Jakupovic, J., Cravotto, G ; Enriù, R.; Varese, M., Bombardelli, E. Tetrahedron Lett. 1995, 36, 3233. For the X-ray crystallographic structure, see: Chiaroni, A ; Riche, C., Marder, R.; Dubois, J., Guénard, D.; Guéritte-Voegelein, F Acta Crystallogr. 1995, C51, 2050.
14. 10-Deacetyl-11,12-dihydrobaccatin III-7-O-TES is described in ref 9, as well as in the following: Appendino, G.; Jakupovic, J., Cravotto, G ; Enriù, R.; Varese, M., Bombardelli, E. Tetrahedron Lett. 1995, 36, 3233. For the X-ray crystallographic structure, see: Chiaroni, A ; Riche, C., Marder, R.; Dubois, J., Guénard, D.; Guéritte-Voegelein, F Acta Crystallogr. 1995, C51, 2050.
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21. While we recognize that a more appropriate trivial nomenclature for this type of structure may be 11,12-dihydro-12,13-dehydrobaccatin III, we prefer and suggest the shortened nomenclature used in this manuscript.
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26. (d) Two groups have reported without comment the formation of a stable enol as a byproduct of taxol total synthesis: Kende, A. S.; Johnson, S.; Sanfilippo, P.; Hodges, J. C.; Jungheim, L. N. J. Am. Chem. Soc. 1986, 108, 3513. Nicolaou, K. C.; Liu, J.-J.; Yang, Z.; Ueno, H.; Sorensen, E. J.; Claiborne, C. F.; Guy, R. K.; Hwang, C.-K.; Nakada, M.; Nanterment, P. G. J. Am. Chem. Soc. 1995, 117, 634.
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31. Cf.: Li, L. H.; et al. Cancer Res. 1992, 52, 4904 We thank Joan W. Culp for the data included here.
32. The results described here were presented at the 210th American Chemical Society National Meeting, Chicago IL, August 20-24, 1995, Abstract Medi 175.
33. The A2780 human ovarian carcinoma cell growth inhibition assay (Lopes, N. M., McGovren, J. P., unpublished results) is based on the cell line described in the following: Perez, R. P., O'Dwyer, P. J.; Handel, L. M.; Ozols, R. F.; Hamilton, T. C. Int. J. Cancer 1991, 48, 265 We thank Narima Lopes and Patrick McGovren for permission to publish these results.
34. The A2780 human ovarian carcinoma cell growth inhibition assay (Lopes, N. M., McGovren, J. P., unpublished results) is based on the cell line described in the following: Perez, R. P., O'Dwyer, P. J.; Handel, L. M.; Ozols, R. F.; Hamilton, T. C. Int. J. Cancer 1991, 48, 265 We thank Narima Lopes and Patrick McGovren for permission to publish these results.