Synthesis of 6α-hydroxypaclitaxel, the major human metabolite of paclitaxel

Tetrahedron Letters

Volumn 39, Issue 28, 1998, Pages 4967-4970

  Yuan, Haiqing ^a   Kingston, David G I ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6ALPHA HYDROXYPACLITAXEL; PACLITAXEL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0032500141     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00970-8     Document Type: Article

References (27)

1. 1. For a review of the development and clinical utility of the taxane class of anticancer agents, see Rowinsky, E. K. Annu. Rev. Med. 1997, 48, 353-374.
2. 2. For reviews of the chemistry and structure-activity relationships of paclitaxel see: (a) Kingston, D. G. I. Pharmac. Ther. 1991, 52, 1-34.
3. (b) Kingston, D. G. I. Trends Biotechnol. 1994, 12, 222-227.
4. (c) Chen, S.-H.; Farina, V. Paclitaxel Structure-Activity Relationships and Core Skeletal Rearrangements. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I.; Chen, T. T.; Ojima, I. and Vyas, D. M., Eds.; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1994; pp 247-261.
5. (d) Georg, G. I.; Boge, T. C.; Cheruvallath, Z. S.; Clowers, J. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. The Medicinal Chemistry of Taxol. In Taxol: Science and Applications; Suffness, M., Ed.; CRC Press, Inc.: Boca Raton, FL, 1995; pp 317-375.
6. (e) Kingston, D. G. I. Recent Advances in the Chemistry and Structure-Activity Relationships of Paclitaxel. In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I.; Chen, T. T.; Ojima, I. and Vyas, D. M., Ed.; American Chemical Society: Washington, DC, 1994; Vol. ACS Symposium Series 583; pp 203-216.
7. (f) Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44.
8. (g) Vyas, D. M.; Kadow, J. F. In Progress in Medicinal Chemistry; Ellis, G. P.; Luscombe, D. K., Ed.; Elsevier Science B. V.: Amsterdam, 1995; Vol. 32; pp 289-337.
9. (h) Guenard, D.; Gueritte-Voegelein, F.; Lavelle, F. Curr. Pharm. Design 1995, 1, 95-112.
10. 3. Rowinsky, E. K.; Wright, M.; Monsarrat, B; Lesser, G.; Donehower, R. C., Cancer Surveys Volume 17: Pharmacokinetics and Cancer Chemotherapy; Imperial Cancer Research Fund, 1993, pp. 283-304.
11. 4. Wright, M.; Monsarrat, B.; Royer, I.; Rowinsky, E. K.; Donehower, R. C.; Cresteil, T.; Guenard, D. In The Chemistry and Pharmacology of Taxol and its Derivatives; Farina, V., Ed.; 1995; Vol. 22; pp 131-164.
12. 5. Vuilhorgne, M.; Gaillard, C.; Sanderink, G. J.; Royer, I.; Monsarrat, B; Dubios, J; Wright, M, ACS Symposium Series 583: Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I.; Chen, T. T.; Ojima, I.; Vyas, D. M., Eds., American Chemical Society, Washington, 1995; pp 98-110.
13. 6. Walle, T.; Kumar, G. N.; McMillan, J. M.; Thornburg, K. R.; Walle, U. K., Biochem. Pharm. 1993, 46, 1661.
14. 7. Monsarrat, B; Mariel, E.; Cros, S.; Gares, M.; Guenard, D.; Gueritte-Voegelein, F.; Wright, M., Drug Metab. Dispos. 1990, 18, 895-904.
15. 8. Harris, J. W.; Katki, A.; Anderson, L. W.; Chmurny, G. N.; Paukstelis, J. V.; Collins, J. M., J. Med. Chem. 1994, 37, 706-709.
16. 9. Kumar, G. N.; Oatis, J. E.; Thornburg, K. R.; Heldrich, F. J.; Hazard, E. S.; Walle, T., Drug Metab. Dispos. 1994, 22, 177-179.
17. 10. Chaudhary, A. G.; Gharpure, M.; Rimoldi, J. M.; Kingston, D. G. I., J. Am. Chem. Soc. 1994, 116, 4097-4098.
18. 11. Nicolaou, K. C.; Renaud, J.; Nantermet, P. G., J. Am. Chem. Soc. 1995, 117, 2409-2420.
19. 12. (a) Holton, R. A.; Biediger, R. J.; Boatman, P. D. In Taxol: Science and Applications; Suffness, M., Ed.; CRC Press, Inc.: Boca Raton, FL, 1995; pp 97-121.
20. (b) Boge, T. C.; Georg, G. I. In Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH, Inc.: New York, 1997; pp 1-43.
21. 13. (a) Liang, X.; Kingston, D. G. I.; Lin, C. M.; Hamel, E. Tetrahedron Lett. 1995, 36, 2901-2904.
22. (b) Liang, X.; Kingston, D. G. I.; Long, B. H.; Fairchild, C. A.; Johnston, K. A. Tetrahedron 1997, 53, 3441-3456.
23. 14. Altstadt, T. J.; Gao, Q.; Wittman, M. D.; Kadow, J. F.; Vyas, D. M. Tetrahedron Lett. 1998, see preceding communication.
24. 13C NMR, HMQC, HMBC, NOESY, and HRFABMS were consistent with the assigned structures (compounds 6 and 7) and with data reported in the literature (compound 1).
25. 16. Fang, W. S.; Fang, Q. C.; Liang, X. T., Syn. Comm. 1997, 27, 2305-2310.
26. 4, and concentrated under reduced pressure. The residue was purified by preparative TLC on silica gel (EtOAc:hexanes 6:4) to give 6 (3.0 mg, 15%) and recovered 5 (16.9 mg, 83%).
27. 18. Castellano, E. E.; Hodder, O. J. R. Acta Cryst. 1973, 529, 2566-2570.