Synthetic studies with 13-deoxybaccatin III

Journal of Organic Chemistry

Volumn 67, Issue 20, 2002, Pages 7140-7143

  Ahn, Yu Mi ^a   Vander Velde, David G ^a   Georg, Gunda I ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHETIC STUDIES;

AMMONIUM COMPOUNDS; OXIDATION; PEROXIDES; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

13 DEOXYBACCATIN 3; 13 EPI 7 O (TRIETHYLSILYL)BACCATIN 3; 4 METHYLMORPHOLINE N OXIDE; MORPHOLINE DERIVATIVE; PACLITAXEL; PEROXIDE; TAXUS BREVIFOLIA EXTRACT; TERT BUTYL PEROXIDE; TETRAPROPYLAMMONIUM PERRUTHENATE; UNCLASSIFIED DRUG;

ARTICLE; CELL CULTURE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; PLANT CELL; REDUCTION; STRUCTURE ANALYSIS;

ALKALOIDS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CHROMATOGRAPHY, THIN LAYER; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXIDATION-REDUCTION; PACLITAXEL; STEREOISOMERISM; TAXOIDS;

EID: 0037020003     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo011183q     Document Type: Article

References (22)

1. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327.
2. Suffness, M.; Wall, M. Discovery and Development of Taxol. In Taxol Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995; pp 3-25.
3. The Chemistry and Pharmacology of Taxol and Its Derivatives; Farina, V., Ed.; Elsevier: Amsterdam, 1995.
4. Spencer, C. M.; Faulds, D. Drugs 1994, 48, 794-847.
5. Kingston, D. G. I. J. Chem. Soc., Chem. Commun. 2001, 867-880.
6. Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Eds.; American Chemical Society: Washington, DC, 1995.
7. Taxol Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995.
8. Denis, J. N.; Greene, A. E.; Guenard, D.; Guéritte-Voegelein, F.; Mangatal, L.; Potier, P. J. Am. Chem. Soc. 1988, 110, 5917-5919.
9. Gi, U.-S.; Min, B.; Hong, S.-S.; Lee, H.-S.; Kim, J.-H. Agric. Chem. Biotechnol. (Engl. Ed.) 2000, 43, 176-179.
10. Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1994, 295-296.
11. Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Sorensen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633.
12. Kingston and co-workers reported compound 5 as the only product when 13β-chloro-13-deoxy-7-O-(triethylsilyl)baccatin III was reacted with sodium azide in DMF. The structure of 5 was identical in all respects to the compound reported in the literature. Chordia, M. D.; Gharpure, M. M.; Kingston, D. G. I. Tetrahedron 1995, 51, 12963-12970.
13. 2. However, starting material was recovered in all cases.
14. Nicolaou and co-workers reported that compound 3 can also be converted to enone 8 by oxidation using excess of pyridiniumchlorochromate (30 equiv) in refluxing benzene (75% yield). See also refs 10 and 11.
15. Salvador, J. A. R.; Sa é Melo, M. L.; Campos Neves, A. S. Tetrahedron Lett. 1997, 38, 119-122.
16. Schultz, A. G.; Wang, A. J. Am. Chem. Soc. 1998, 120, 8259-8260.
17. Chidambaram, N.; Chandrasekaran, S. J. Org. Chem. 1987, 52, 5048-5051.
18. Matsusita, Y.; Sugamoto, K.; Matsui, T. Chem. Lett. 1993, 925-928.
19. Keck, G. E.; McHardy, S. F.; Wager, T. T. Tetrahedron Lett. 1995, 36, 7419-7422.
20. Hoemann, M. Z.; Vander Velde, D. G.; Aubé, J.; Georg, G. I.; Jayasinghe, L. R. J. Org. Chem. 1995, 60, 2918-2921.
21. Treatment of 9 with diethyl azodicarboxylate (DEAD), trimethylphosphine, and chloroacetic acid (or p-nitrobenzoic acid) in toluene at 90°C resulted in the formation of elimination product 6 instead of providing baccatin III 10 (Scheme 2). Other conditions for the Mitsunobu reaction of 9 were investigated ((a) triphenylphosphine, p-nitrobenzoic acid, DEAD, at room temperature in THF;(b)triphenylphosphine, p-nitrobenzoic acid, DEAD, at 90°C in toluene;(c) trimethylphosphine, p-nitrobenzoic acid, DEAD, at room temperature in THF)
22. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693-2698.