Synthesis of docetaxel and butitaxel analogues through kinetic resolution of racemic β-lactams with 7-O-triethylsilylbaccatin III

Journal of Organic Chemistry

Volumn 72, Issue 3, 2007, Pages 756-759

  Ge, Haibo ^a   Spletstoser, Jared T ^a   Yang, Yan ^b   Kayser, Margaret ^b   Georg, Gunda I ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b UNIVERSITY OF NEW BRUNSWICK   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DOCETAXELS; KINETIC RESOLUTIONS; LACTAMS; PACLITAXELS;

DERIVATIVES; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

4 PHENYL 3 HYDROXY BETA LACTAM DERIVATIVE; 4 TERT BUTYL 3 HYDROXY BETA LACTAM DERIVATIVE; 7 O TRIETHYLSILYLBACCATIN III; BACCATIN III; BETA LACTAM DERIVATIVE; BUTITAXEL DERIVATIVE; DOCETAXEL DERIVATIVE; TAXANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; RACEMIC MIXTURE; STEREOCHEMISTRY;

ALKALOIDS; ANTINEOPLASTIC AGENTS; BETA-LACTAMS; KINETICS; MODELS, CHEMICAL; STEREOISOMERISM; TAXOIDS;

EID: 33846910250     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061339s     Document Type: Article

References (26)

1. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327.
2. For review: Zhou, J.; Giannakakou, P. Curr. Med. Chem.: Anti-Cancer Agents 2005, 5, 65-71.
3. For review: Spencer, C. M.; Faulds, D. Drugs 1994, 48, 794-847.
4. Ge, H.; Vasandani, V.; Huff, J. K.; Audus, K. L.; Himes, R. H.; Seelig, A.; Georg, G. I. Bioorg. Med. Chem. Lett. 2006, 16, 433-436.
5. For review: Kingston, D. G. I.; Jagtap, P. G.; Yuan, H.; Samala, L. Prog. Chem. Org. Nat. Prod. 2002, 84, 53-225.
6. Ali, S. M.; Hoemann, M. Z.; Aube, J.; Mitscher, L. A.; Georg, G. I.; McCall, R.; Jayasinghe, L. R. J. Med. Chem. 1995, 38, 3821-3828.
7. Ali, S. M.; Hoemann, M. Z.; Aubé, J.; Georg, G. I.; Mitscher, L. A. J. Med. Chem. 1997, 40, 236-241.
8. Mastalerz, H.; Cook, D.; Fairchild, C. R.; Hansel, S.; Johnson, W.; Kadow, J. F.; Long, B. H.; Rose, W. C.; Tarrant, J.; Wu, M.-J.; Xue, M.-Q.; Zhang, G.-F.; Zoeckler, M.; Vyas, D. M. Bioorg. Med. Chem. 2003, 11, 4315-4323.
9. Rice, A.; Liu, Y.; Michaelis, M. L.; Himes, R. H.; Georg, G. I.; Audus, K. J. Med. Chem. 2005, 48, 832-838.
10. For review: Boge, T. C.; Georg, G. I. The Medicinal Chemistry of β-Amino Acids: Paclitaxel as an Illustrative Example. In Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; pp 1-43.
11. Kayser, M. M.; Mihovilovic, M. D.; Kearns, J.; Feicht, A.; Stewart, J. D. J. Org. Chem. 1999, 64, 6603-6608.
12. Kayser, M. M.; Yang, Y.; Mihovilovic, M. D.; Feicht, A.; Rochon, F. D. Can. J. Chem. 2002, 80, 796-800.
13. Yang, Y.; Wang, F.-Y.; Rochon, F. D.; Kayser, M. M. Can. J. Chem. 2005, 83, 28-36.
14. Patel, R. N.; Howell, J.; Chidambaram, R.; Benoit, S.; Kant, J. Tetrahedron: Asymmetry 2003, 14, 3673-3677.
15. Carr, J. C.; Al-Azemi, T. F.; Long, T. E.; Shim, J.-Y.; Coates, C. M.; Turos, E.; Bisht, K. S. Tetrahedron 2003, 59, 9147-9160.
16. Holton, R. A.; Biedinger, R. J.; Boatman, P. D. Semisynthesis of Taxol and Taxotere. In Taxol Science and Applications; Suffness, M., Ed.; CRC: Boca Raton, FL, 1995; pp 97-121.
17. Ojima, I.; Slater, J. C. Chirality 1997, 9, 487-494.
18. Takeda, Y.; Uoto, K.; Iwahana, M.; Jimbo, T.; Nagata, M.; Atsumi, R.; Ono, C.; Tanaka, N.; Terasawa, H.; Soga, T. Bioorg. Med. Chem. Lett. 2004, 14, 3209-3215.
19. Yang, Y.; Drolet, M.; Kayser, M. M. Tetrahedron: Asymmetry 2005, 16, 2748-2753.
20. Lin, S.-N.; Geng, X.-D.; Qu, C.-X.; Tynebor, R.; Gallagher, D. J.; Pollina, E.; Rutter, J.; Ojima, I. Chirality 2000, 12, 431-441.
21. Spletstoser, J. T.; Flaherty, P. T.; Himes, R. H.; Georg, G. I. J. Med. Chem. 2004, 47, 6459-6465.
22. Georg, G. I.; Kant, J.; Gill, H. J. J. Am. Chem. Soc. 1987, 109, 1129-1135.
23. Denis, J.-N.; Greene, A. E.; Guénard, D.; Gu'eritte-Voegelein, F.; Mangatal, L.; Potier, P. J. Am. Chem. Soc. 1988, 110, 5917-5919.
24. Ojima, I.; Sun, C.-M.; Zucco, M.; Park, Y. H.; Duclos, O.; Kuduk, S. Tetrahedron Lett. 1993, 34, 4149-4152.
25. Mangatal, L.; Adeline, M.-T.; Guénard, D.; Guéritte- Voegelein, F.; Potier, P. Tetrahedron 1989, 45, 4177-4190.
26. Compound 9 showed spectroscopic properties in agreement with the data reported: Holton, R. A.; Chai, K.-B.; Idmoumaz, H.; Nadizadeh, H.; Rengan, K.; Suzuki, Y.; Tao, C. U.S. Pat. 5739362, 1998.