New skeletal rearrangements of C and D rings of a 13-oxobaccatin III derivative

Tetrahedron

Volumn 54, Issue 52, 1998, Pages 15833-15844

  Marder Karsenti, Raphaële ^a   Dubois, Joëlle ^a   Chiaroni, Angèle ^a   Riche, Claude ^a   Guénard, Daniel ^a   Guéritte, Françoise ^a   Potier, Pierre ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

13 OXOBACCATIN III; 13 OXOBACCATIN III DERIVATIVE; 7,13 DIOXO SECOBACCATIN III; DOCETAXEL; PACLITAXEL; PACLITAXEL DERIVATIVE; TAXOID; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0032564580     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00993-4     Document Type: Article

References (35)

1. [1] Wani, M.C.; Taylor, H.L.; Wall, M.E.; Coggon, P.; McPhail, A.T. J. Am. Chem. Soc. 1971, 93, 2325
2. [2] For review : Guénard, D.; Guéritte-Voegelein, F.; Potier, P.. Acc. Chem. Res. 1993. 26, 160
3. [3] (a) Schiff, P.B.; Fant, J.; Horwitz, S.B. Nature 1979, 277, 665.
4. (b) Schiff, P.B.; Horwitz, S.B. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 1561
5. [4] For general reviews on taxoid chemistry see: (a)Taxol: Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995;
6. (b) Taxane Anticancer Agents: Basic Science and Current Status Georg, I.G.; Chen, T.T.; Ojima, I.; Vyas, D.M. Eds.; ACS Symposium Series No 583, American Chemical Society, Washington D.C. 1995;
7. (c) The Chemistry and Pharmacology of Taxol® and its Derivatives Farina V. Ed.; Elsevier, 1995
8. [5] (a) Chen, S.-H.; Farina, V. Paclitaxel Structure-Activity Relationships and Skeletal Rearrangements. InTaxane Anticancer Agents: Basic Science and Current Status Georg, I.G.; Chen, T.T.; Ojima, I.; Vyas, D.M. Eds.; ACS Symposium Series No 583, American Chemical Society, Washington D.C., 1995; pp 247-261 and references therein
9. (b) Chen, S.-H.; Farina, V. Paclitaxel (Taxol®) Chemistry and Structure-Activity Relationships. In The Chemistry and Pharmacology of Taxol® and its Derivatives Farina V. Ed.; Elsevier, 1995, pp 165-253 and references therein.
10. [6] Appendino, G.; Jakupovic, J.; Cravotto, G.; Enriù, R.; Varese, M.; Bombardelli, E. Tetrahedron Lett. 1995, 36, 3233-3236
11. [7] Liang, X.; Kingston, D.G.I.; Long, B.H.; Fairchild, C.A.; Johnston, K.A. Tetrahedron Lett. 1995, 36, 7795-7798
12. [8] Chen, S.-H.; Huang, S.; Roth, G.P. Tetrahedron Lett. 1995, 36, 8933-8936
13. [9] Pinciroli, V.; Ceccarelli, W.; Fusar-Bassini, D.; Menichincheri, M.; Mongelli, N.; Vanotti, E. Tetrahedron Lett. 1996, 37, 9365-9368
14. [10] Yu, C.-Z.; Liu, Z.-Y. Tetrahedron Lett. 1997, 38, 4133-4136
15. [11] Appendino, G.; Danieli, B.; Jakupovic, Belloro, E.; Scambia, G.; Bombardelli, E. Tetrahedron Lett. 1997, 38, 4273-4276
16. [12] Appendino, G.; Fenoglio, I. Vander Velde, D.G. J. Nat. Prod. 1997, 60, 464-466
17. [13] Liang, X.; Kingston, D.G.I.; Long, B.H.; Fairchild, C.A.; Johnston, K.A. Tetrahedron 1997, 53, 3441-3456
18. [14] Wender, P.A.; Lee, D.; Lai, T.K.; Horwitz, S.B.; Rao, S. Biorg. Med. Chem. Lett. 1997, 7, 1941-1944
19. [15] Ojima, I.; Lin, S.; Chakravarrty, S.; Fenoglio, I.; Park, Y.H.; Sun, C.-M.; Appendino, G.; Pera, P.; Veith, J.M.; Bernacki, R.J. J. Org. Chem. 1998, 63, 1637-1645
20. [16] Marder-Karsenti, R. Réactivité chimique des taxoïdes: Modifications structurales des cycles A et D. Ph D Thesis, Université Paris VI, 1996
21. [17] Marder-Karsenti, R.; Dubois, J.; Bricard, L.; Guénard, D.; Guéritte, F. J. Org. Chem. 1997, 62, 6631-6637
22. [18] Magri, N.F.; Kingston, D.G.I. J. Org. Chem. 1986, 51, 797-802
23. [19] 13-oxobaccatin III was first described in ref 1.
24. [20] Guéritte-Voegelein, F.; Guénard, D.; Dubois, J.; Wahl, A.; Marder, R.; Müller, R.; Lund, M.; Bricard, L.; Potier, P. in Taxane Anticancer Agents: Basic Science and Current Status Georg, I.G.; Chen, T.T.; Ojima, I.; Vyas, D.M. Eds.; ACS Symposium Series No 583, American Chemical Society, Washington D.C., 1995; pp 189-202
25. [21] (a) Appendino, G.; Jakupovic, J.; Varese, M.; Bombardelli, E. Tetrahedron Lett. 1996, 37, 727-730;
26. (b) Zamir, L.O.; Balachandran, S.; Zheng, Y.F.; Nedea, M.E.; Caron, G.; Nikolakakis, A.; Vishwakarma, R.A.; Sauriol, F.; Mamer, O. Tetrahedron, 1997, 53, 15991-16008
27. [22] Anh, N.T.; Thanh, B.T. New J. Chem. 1986, 10, 681-683
28. [23] Chaudary A.G.; Chordia, M.D.; Kingston, D.G.I. J. Org. Chem. 1995, 60, 3260-3262
29. [24] Nagata, W.; Hirai, S.; Itazaki, H.; Takeda, K. J. Org. Chem. 1963, 26, 2413-2421
30. [25] Nagata, W.; Yoshioka, M.; Hirai, S. J. Am. Chem. Soc. 1972, 94, 4635-4643
31. [26] Nagata, W.; Narisada, M.; Sugasawa, T. J. Chem. Soc. (C) 1967, 648-660
32. [27] Sheldrick, G.M. 1986 SHELXS86. Program for the solution of crystal structures. Univ. of Göttingen, Germany.
33. [28] Sheldrick, G.M. 1993 SHELXL93. Program for the refinement of crystal structures. Univ. of Göttingen, Germany.
34. [29] Marder, R.; Dubois, J.; Guénard, D.; Guéritte-Voegelein, F.; Potier, P. Tetrahedron 1995, 51, 1985-1994
35. [30] Chauvière, G.; Guénard, D.; Picot, F.; Sénihl, V.;Potier, P. C. R. Acad. Sc. Paris 1981, 293, 501