A highly efficient, practical approach to natural taxol

Journal of the American Chemical Society

Volumn 110, Issue 17, 1988, Pages 5917-5919

  Denis, Jean Noël ^a   Greene, Andrew E ^a   Guénard, Daniel ^b   Guéritte Voegelein, Françoise ^b   Mangatal, Lydie ^b   Potier, Pierre ^b  

^a UNIV GRENOBLE ALPES   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

TAXOL;

DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PRELIMINARY COMMUNICATION;

EID: 0023678710     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00225a063     Document Type: Article

References (12)

1. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325–2327.
2. Taxol (NSC-125973) is currently in phase II clinical trials in the United States. It is the only plant product known to promote the assembly of microtubules and inhibit the tubulin disassembly process and, thus, appears to be the prototype of a new class of cancer chemotherapeutic agents. See: Suffness, M.; Cordell, G. A. In The Alkaloids, Chemistry and Pharmacology, Brossi, A., Ed.; Academic Press: Orlando, FL, 1985; Vol. XXV, Chapter 1
3. Douros, J.; Suffness, M. In Recent Results in Cancer Research; Carter, S. K., Sakurai, Y., Umezawa, H., Eds.; Spinger-Verlag: Berlin, 1981; Vol. 76, pp 169–170. Lomax, N. R.; Narayanan, V. L. Chemical Structures of Interest to the Division of Cancer Treatment; U.S. Government Printing Office: Washington, D.C., 1983; Vol. III, p 17. Engel, S. I.; Schwartz, E. L.; Strauman, J. J.; Wiernik, P. H. Proc. Am. Assoc. Cancer Res. 1985, 26, 158. Zee-Cheng, R. K.-Y.; Cheng, C. C. Drugs of the Future 1986, 11, 45–48.
4. Miller, R. W.; Powell, R. G.; Smith, C. R., Jr.; Arnold, E.; Clardy, J. J. Org. Chem. 1981, 46, 1469–1474. (b) Sénilh, V.; Blechert, S.; Colin, M.; Guénard, D.; Picot, F.; Potier, P.; Varenne, P. J. Nat. Prod. 1984, 47, 131–137. (c) Magri, N. F.; Kingston, D. G. I. J. Org. Chem. 1986, 51, 797–802. (d) See, also: Sénilh, V. Ph.D. Dissertation, Université de ParisSud, Orsay, 1984, and references cited therein.
5. 7
6. Suffness, M. National Cancer Institute, personal communication.
7. r. F.; Amarasekara, A. S.; Perumattam, J. J. J. Org. Chem. 1987, 52, 1119–1124. For more recent work, see: Swindell, C. S.; Patel, B. P.; deSolms, S. J. J. Org. Chem. 1987, 52, 2346–2355. Hua, D. H.; Gung, W. Y. Ostrander, R. A.; Takusagawa, F. J. Org. Chem. 1987, 52, 2509–2517. Lin, J.; Nikaido, M. M.; Clark, G, J. Org. Chem. 1987, 52, 3745–3752. Wender, P. A.; Snapper, M. L, Tetrahedron Lett. 1987, 28, 2221–2224, Pettersson, L.; Frejd, T.; Magnusson, G. Tetrahedron Lett. 1987, 28, 2753–2756. Swindell, C. S.; Patel, B. P. Tetrahedron Lett. 1987, 28, 5275–5278. Bonnert, R. V.; Jenkins, P. R. J. Chem. Soc., Chem. Commun. 1987, 1540–1541. Shea, K. J.; Haffner, C. D. Tetrahedron Lett. 1988, 29, 1367–1370. Trost, B. M.; Fray, M. J. Tetrahedron Lett. 1988, 29, 2163–2166.
8. Chauviére, G.; Guénard, D.; Picot, F.; Sénilh, V.; Potier, P. C. R. Seances Acad. Sci., Ser 2 1981, 293, 501–503. We are currently obtaining 2 in yields of ca. 1 g/kg of fresh leaves. (It should be noted that 2 is far less active than taxol.) For previous transformations of 2, including an alternative approach to taxol, see references 12a,b and Colin, M.; Guénard, D.; Guéritte-Voegelein, F.; Potier, P. French Patent 2 601 676, 1986.
9. Kingston, D. G. I. Virginia Polytechnic Institute and State University, personal communication.
10. See: (a) Sénilh, V.; Guéritte, F.; Guénard, D.; Colin, M.; Potier, P. C. R. Seances Acad. Sci., Ser 2 1984, 299, 1039–1043. (b) Guéritte-Voegelein, F.; Sénilh, V.; David, B.; Guénard, D.; Potier, P. Tetrahedron 1986, 42, 4451–4460. (c) Magri, N. F.; Kingston, D. G. I.; Jitrangsri, C.; Piccariello, T. J. Ore. Chem. 1986, 51, 3239–3242.
11. See: Denis, J.-N.; Greene, A. E.; Serra, A. A.; Luche, M.-J. J. Org. Chem. 1986, 51, 46–50. A methoxymethyl protecting group at C-2'could not be removed following esterification. The more acid-sensitive ethoxyethyl group, while inherently unstable due to the adjacent (acidic) carboxyl group, was sufficiently resistant to permit 5 to be isolated and used in the esterification. (At -20 °C in toluene, 5 can be kept for several days without appreciable change.) Cf.: Begley, M. J.; Cameron, A. G.; Knight, D. W. J. Chem. Soc., Chem. Commun. 1984, 827–829. Walkup, R. D.; Cunningham, R. T, Tetrahedron Lett. 1987, 28, 4019–4022.
12. Based on 50% conversion. At 85% conversion, the yield is 60%. This procedure is a substantial modification of Kim general esterification method (Kim, S.; Lee, J. I.; Ko, Y. K. Tetrahedron Lett. 1984, 25, 4943–4946), which failed to produce any 4 at all under the published reaction conditions. In that C-13 cinnamoylation also proceeds in remarkably high yield (>90% isolated yield), this procedure appears to be general.