Concise means for accessing an advanced precursor to 1-deoxypaclitaxel

Journal of Organic Chemistry

Volumn 70, Issue 1, 2005, Pages 315-320

  Guo, Xin ^a   Paquette, Leo A ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; HYDRIDES; KETONES;

STEREOSELECTIVITY; TRANSANNULAR HYDRIDES;

ORGANIC COMPOUNDS;

1 DEOXYPACLITAXEL; ALCOHOL; DIKETONE; KETOL; PACLITAXEL DERIVATIVE; UNCLASSIFIED DRUG;

ACETALIZATION; ACETYLATION; ARTICLE; CHEMICAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERIZATION; PRECURSOR; SEQUENTIAL ANALYSIS; STEREOCHEMISTRY; WAGNER MEERWEIN REARRANGEMENT;

COMBINATORIAL CHEMISTRY TECHNIQUES; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PACLITAXEL; STEREOISOMERISM;

EID: 11844305932     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048289g     Document Type: Article

References (37)

1. (a) Taxol: Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995.
2. (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, 1995.
3. (c) The Chemistry and Pharmacology of Taxol and its Derivatives; Farina, V., Ed.; Elsevier: Oxford, 1995.
4. (a) Samaranayake, G.; Magri, N. F.; Jitrangsri, C.; Kingston, D. G. I. J. Org. Chem. 1991, 56, 5114.
5. (b) Chordia, M. D.; Kingston, D. G. I.; Hamel, E.; Lin, C. M.; Long, B. H.; Fairchild, C. A.; Johnston, K. A.; Rose, W. C. Bioorg. Med. Chem. 1997, 5, 941.
6. (c) Chordia, M. D.; Kingston, D. G. I. Tetrahedron 1997, 53, 5699.
7. Wahl, A.; Guéritte-Voegelein, G.; Guénard, D.; LeGoff, M.; Potier, P. Tetrahedron 1992, 48, 6965.
8. Chen, S. H.; Huang, S.; Wei, J.; Farina, V. J. Org. Chem. 1993, 58, 4520.
9. Appendino, G.; Varese, M.; Gariboldi, P.; Gabetta, B. Tetrahedron Lett. 1994, 35, 2217.
10. (a) Kingston, D. G. I.; Molinero, A. A.; Rimoldi, J. M. Prog. Chem. Org. Nat. Prod. 1993, 61, 1.
11. (b) Kingston, D. G. I.; Jagtap, P. G.; Yuan, H.; Samala, L. Prog. Chem. Org. Nat. Prod. 2002, 84, 53.
12. (a) Paquette, L. A.; Zhao, M.; Montgomery, F.; Zeng, Q.; Wang, T. Z.; Elmore, S.; Combrink, K.; Wang, H.-L.; Bailey, S.; Su, Z. Pure Appl. Chem. 1998, 70, 1449.
13. (b) Paquette, L. A.; Hofferberth, J. E. J. Org. Chem. 2003, 68, 2266.
14. Paquette, L. A.; Lo, H. Y. J. Org. Chem. 2003, 68, 2282.
15. Brennan, N.; Guo, X.; Paquette, L. A. J. Org. Chem. 2005, 70, In press (JO0482965).
16. Paquette, L. A.; Hofferberth, J. E. Org. React. 2003, 62, 477.
17. (a) Paquette, L. A.; Elmore, S. W.; Combrink, K. D.; Hickey, E. R.; Rogers, R. D. Helv. Chim. Acta 1992, 75, 1755.
18. (b) Paquette, L. A.; Combrink, K. D.; Elmore, S. W.; Zhao, M. Helv. Chim. Acta 1992, 75, 1772.
19. (c) Paquette, L. A.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5203.
20. (d) Paquette, L. A.; Wang, H.; Su, Z.; Zhao, M. J. Am. Chem. Soc. 1998, 120, 5213.
21. Holton, R. A.; Tang, S.; Liang, F.; Somoza, C. PCT Int. Appl. WO 42, 181, 1997.
22. Benigni, D.; Dillon, J.; Weaver, D.; Haines, K.; Shultis, K.; Focigle, G.; Lin, H.-Y.; Rourick, R.; Crull, G.; Huang, S.; Baumes, J.; Long, B.; Fairchild, C. 41st Annual Meeting of the American Chemical Society of Pharmacognosy, Seattle, WA, July 22-26, 2000. Abstract P-16.
23. Hofferberth, J. E.; Lo, H. Y.; Paquette, L. A. Org. Lett. 2001, 3, 1777.
24. For selected examples, see: (a) Maruoka, K.; Hasegawa, M.; Yamamoto, H. J. Am. Chem. Soc. 1986, 108, 3827. (b) Tu, Y. Q.; Fan, C. A.; Ren, S. K.; Chan, A. S. C. J. Chem. Soc., Perkin Trans. 1 2000, 3792. (c) Wang, F.; Tu, Y. Q.; Fan, C. A.; Wang, S. H.; Zhang, F. M. Tetrahedron: Asymmetry 2002, 13, 395. (d) Tanino, K.; Onuki, K.; Asano, K.; Miyashita, M.; Nakamura, T., Takahashi, Y.; Kuwajima, I. J. Am. Chem. Soc. 2003, 125, 1498.
25. For selected examples, see: (a) Maruoka, K.; Hasegawa, M.; Yamamoto, H. J. Am. Chem. Soc. 1986, 108, 3827. (b) Tu, Y. Q.; Fan, C. A.; Ren, S. K.; Chan, A. S. C. J. Chem. Soc., Perkin Trans. 1 2000, 3792. (c) Wang, F.; Tu, Y. Q.; Fan, C. A.; Wang, S. H.; Zhang, F. M. Tetrahedron: Asymmetry 2002, 13, 395. (d) Tanino, K.; Onuki, K.; Asano, K.; Miyashita, M.; Nakamura, T., Takahashi, Y.; Kuwajima, I. J. Am. Chem. Soc. 2003, 125, 1498.
26. For selected examples, see: (a) Maruoka, K.; Hasegawa, M.; Yamamoto, H. J. Am. Chem. Soc. 1986, 108, 3827. (b) Tu, Y. Q.; Fan, C. A.; Ren, S. K.; Chan, A. S. C. J. Chem. Soc., Perkin Trans. 1 2000, 3792. (c) Wang, F.; Tu, Y. Q.; Fan, C. A.; Wang, S. H.; Zhang, F. M. Tetrahedron: Asymmetry 2002, 13, 395. (d) Tanino, K.; Onuki, K.; Asano, K.; Miyashita, M.; Nakamura, T., Takahashi, Y.; Kuwajima, I. J. Am. Chem. Soc. 2003, 125, 1498.
27. For selected examples, see: (a) Maruoka, K.; Hasegawa, M.; Yamamoto, H. J. Am. Chem. Soc. 1986, 108, 3827. (b) Tu, Y. Q.; Fan, C. A.; Ren, S. K.; Chan, A. S. C. J. Chem. Soc., Perkin Trans. 1 2000, 3792. (c) Wang, F.; Tu, Y. Q.; Fan, C. A.; Wang, S. H.; Zhang, F. M. Tetrahedron: Asymmetry 2002, 13, 395. (d) Tanino, K.; Onuki, K.; Asano, K.; Miyashita, M.; Nakamura, T., Takahashi, Y.; Kuwajima, I. J. Am. Chem. Soc. 2003, 125, 1498.
28. (a) Johnston, J. N.; Tsui, H.-C.; Paquette, L. A. J. Org Chem. 1998, 63, 129.
29. (b) Zeng, Q.; Bailey, S.; Wang, T. Z.; Paquette, L. A. J. Org. Chem. 1998, 63, 137.
30. Rossiter, B. E. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.-in-Chief; Wiley: Chichester, 1995; Vol. 8, p 5479.
31. Paquette, L. A.; Lo, H. Y.; Hofferberth, J. E.; Gallucci, J. C. J. Org. Chem. 2003, 68, 2276.
32. (a) Donohoe, T. J.; Moore, P. R.; Waring, M. J.; Newcombe, N. J. Tetrahedron Lett. 1997, 38, 5027.
33. (b) Donohoe, T. J.; Blades, K.; Moore, P. R.; Waring, M. J.; Winter, J. J. G.; Helliwell, M.; Newcombe, N. J.; Stemp, G. J. Org. Chem. 2002, 67, 7946.
34. Guo, X. Unpublished observations from this laboratory.
35. Stirmer, R.; Ritter, K.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 105.
36. (a) Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703.
37. (b) Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919.