Catalytic asymmetric aminohydroxylation provides a short taxol side-chain synthesis

Acta Chemica Scandinavica

Volumn 50, Issue 8, 1996, Pages 649-651

  Li, Guigen ^a   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4-TOLUENESULFONAMIDE; CINNAMIC ACID DERIVATIVE; CINNAMIC ACID METHYL ESTER; DRUG DERIVATIVE; PACLITAXEL; SULFONAMIDE; TOLUENE; TOLUENESULFONAMIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROXYLATION; SYNTHESIS;

CINNAMATES; HYDROXYLATION; MOLECULAR STRUCTURE; PACLITAXEL; SULFONAMIDES; TOLUENE;

EID: 0030215491     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.50-0649     Document Type: Article

References (23)

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5. For the latest modifications of the Taxol side-chain see: (a) Nicolaou, K. C., Guy, R. K., Pitsinos, E. N. and Wrasidlo, W. Angew. Chem., Int. Ed Engl. 33 (1994) 1583 (b) Syed M. Ali Hoemann, M. Z., Aube, J., Mitscher, L. A., Georg, G. I., McCall, R. and Jayasinghe, L. R. J. Med. Chem. 38 (1995) 3821 (c)Ojima, I., Duclos, O., Dorman, G., Simonot, B., Prestiwich, G. D., Rao, S., Lerro, K. A. and Horwitz, S. B. J. Med Chem. 38 (1995) 3891 (d) Bourzat, J.-D., Lavelle, F. and Commercon, A. Biomed. Chem. Lett. 5 (1995) 809.
6. For the latest modifications of the Taxol side-chain see: (a) Nicolaou, K. C., Guy, R. K., Pitsinos, E. N. and Wrasidlo, W. Angew. Chem., Int. Ed Engl. 33 (1994) 1583 (b) Syed M. Ali Hoemann, M. Z., Aube, J., Mitscher, L. A., Georg, G. I., McCall, R. and Jayasinghe, L. R. J. Med. Chem. 38 (1995) 3821 (c)Ojima, I., Duclos, O., Dorman, G., Simonot, B., Prestiwich, G. D., Rao, S., Lerro, K. A. and Horwitz, S. B. J. Med Chem. 38 (1995) 3891 (d) Bourzat, J.-D., Lavelle, F. and Commercon, A. Biomed. Chem. Lett. 5 (1995) 809.
7. For the latest modifications of the Taxol side-chain see: (a) Nicolaou, K. C., Guy, R. K., Pitsinos, E. N. and Wrasidlo, W. Angew. Chem., Int. Ed Engl. 33 (1994) 1583 (b) Syed M. Ali Hoemann, M. Z., Aube, J., Mitscher, L. A., Georg, G. I., McCall, R. and Jayasinghe, L. R. J. Med. Chem. 38 (1995) 3821 (c)Ojima, I., Duclos, O., Dorman, G., Simonot, B., Prestiwich, G. D., Rao, S., Lerro, K. A. and Horwitz, S. B. J. Med Chem. 38 (1995) 3891 (d) Bourzat, J.-D., Lavelle, F. and Commercon, A. Biomed. Chem. Lett. 5 (1995) 809.
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14. (b) The first, albeit inefficient, catalytic asymmetric aminohydroxylations were performed by C. J. Burns and D. Gilheanny in the author's laboratory at Massachusetts Institute of Technology in 1987. Unpublished results
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19. for latest developments on deprotection of arylsulfonamides see: (c) Fukuyama, T., Jow, C.-K. and Cheung, M. Tetrahedron Lett. 36 (1995) 6376 (d) Goulaouic-Dubois, C., Guggisberg, A. and Hesse, M. J. Org. Chem. 60 (1995) 5969 (e) Vedejs, E. and Lin, S. J. Org. Chem. 59 (1994) 1602.
20. for latest developments on deprotection of arylsulfonamides see: (c) Fukuyama, T., Jow, C.-K. and Cheung, M. Tetrahedron Lett. 36 (1995) 6376 (d) Goulaouic-Dubois, C., Guggisberg, A. and Hesse, M. J. Org. Chem. 60 (1995) 5969 (e) Vedejs, E. and Lin, S. J. Org. Chem. 59 (1994) 1602.
21. T.-J. Xiang, SepraChem. Personal communication.
22. Assumed to be ca. 92% ee since no enrichment is anticipated in this hydrolysis step.
23. -1, 21.7 min (2R,3S), 24.9 min (2S,3R).