An Improved Synthesis of the Taxol Side Chain and of RP 56976

Journal of Organic Chemistry

Volumn 55, Issue 6, 1990, Pages 1957-1959

  Denis, Jean Noel ^a   Correa, Arlene ^a   Greene, Andrew E ^a  

^a UNIV GRENOBLE ALPES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 19644376049     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00293a052     Document Type: Article

References (23)

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2. Taxol (NSC-125973) is currently in phase II clinical trials in the United States. See: 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.
3. Suffness, M.; Cordell, G. A. In The Alkaloids, Chemistry and. Pharmacology, Brossi, A., Ed.; Academic Press: Orlando, FL, 1985; Vol. XXV, Chapter 1.
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6. For a compilation of recent references, see: Neh, H.; Kuhling, A.; Blechert, S. Helv. Chim. Acta 1989, 72, 101–109. For earlier work, see ref 5.
7. Although partial kinetic resolution has been observed, it would appear too modest to be preparatively useful. See: Mangatal, L. Ph.D. Dissertation, Universite de Paris-Sud, Orsay, 1989.
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10. Serra, A. A. Ph.D. Dissertation, Universite Scientifique, Techno-logique et Medicale de Grenoble, 1987.
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12. Eur. Pat. Appl. EP 253,738, 1988.
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14. Guéritte-Voegelein, F.; Guenard, D.; Mangatal, L.; Potier, P.; Guilhem, J.; Cesario, M.; Pascard, C. Acta Crystallogr., submitted for publication. See also ref 3.
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18. The enantiomeric excesses were determined by HPLC analysis of the derived diacetates (Pirkle phenylglycine column and acetonitrile-2-propanol-heptane solvent system). We thank Dr. Mulhauser (Rhone-Poulenc Recherches) for these determinations.
19. See: Pimentel, G. C.; McClellan, A. L. The Hydrogen Bond; W. H. Freeman and Company: San Francisco, 1960; Chapter 5.
20. For an explanation of this effect, see: Mouloungui, Z.; Delmas, M.; Gaset, A. J. Org. Chem. 1989, 54, 3936–3941.
21. Behrens, C. H.; Sharpless, K. B. Aldrichimica Acta 1983, 16, 67–79.
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