The pinene path to taxanes. 4. Approaches to taxol and taxol analogs through elaboration of aromatic C-ring precursors

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7662-7663

  Wender, Paul A ^a   Glass, Timothy E ^a   Krauss, Nancy E ^a   Mühlebach, Michel ^a   Peschke, Bernd ^a   Rawlins, David B ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TAXANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029847589     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961289z     Document Type: Article

References (20)

1. Taxol is the registered trademark for the molecule with generic name paclitaxel. For a recent review of synthetic studies from over 35 groups, see: (a) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL® Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. For overviews of other aspects of taxol research, see: (b) Taxane Anticancer Agents: Basic Science and Current Status; Georg, G., Chen, T., Ojima, I., Vyas, D., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC, 1995. For total syntheses of Taxol, see: (c) Holton, R. A.; Somoza, C.; Kim, H. B.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1597-1598, 1599-1600. (d) Nicolaou, K. C.; Yang, Z.; Ueno, H.; Nantermet, P. G.; Guy, R. K.; Claiborne, C. F.; Renaud, J.; Couladouros, E. A.; Paulvannan, K.; Sorensen, E. J. Nature 1994, 367, 630. (e) Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, J. J. Am. Chem. Soc. 1996, 118, 2843-2859 and references cited therein.
2. Taxol is the registered trademark for the molecule with generic name paclitaxel. For a recent review of synthetic studies from over 35 groups, see: (a) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL® Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. For overviews of other aspects of taxol research, see: (b) Taxane Anticancer Agents: Basic Science and Current Status; Georg, G., Chen, T., Ojima, I., Vyas, D., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC, 1995. For total syntheses of Taxol, see: (c) Holton, R. A.; Somoza, C.; Kim, H. B.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1597-1598, 1599-1600. (d) Nicolaou, K. C.; Yang, Z.; Ueno, H.; Nantermet, P. G.; Guy, R. K.; Claiborne, C. F.; Renaud, J.; Couladouros, E. A.; Paulvannan, K.; Sorensen, E. J. Nature 1994, 367, 630. (e) Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, J. J. Am. Chem. Soc. 1996, 118, 2843-2859 and references cited therein.
3. Taxol is the registered trademark for the molecule with generic name paclitaxel. For a recent review of synthetic studies from over 35 groups, see: (a) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL® Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. For overviews of other aspects of taxol research, see: (b) Taxane Anticancer Agents: Basic Science and Current Status; Georg, G., Chen, T., Ojima, I., Vyas, D., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC, 1995. For total syntheses of Taxol, see: (c) Holton, R. A.; Somoza, C.; Kim, H. B.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1597-1598, 1599-1600. (d) Nicolaou, K. C.; Yang, Z.; Ueno, H.; Nantermet, P. G.; Guy, R. K.; Claiborne, C. F.; Renaud, J.; Couladouros, E. A.; Paulvannan, K.; Sorensen, E. J. Nature 1994, 367, 630. (e) Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, J. J. Am. Chem. Soc. 1996, 118, 2843-2859 and references cited therein.
4. Taxol is the registered trademark for the molecule with generic name paclitaxel. For a recent review of synthetic studies from over 35 groups, see: (a) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL® Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. For overviews of other aspects of taxol research, see: (b) Taxane Anticancer Agents: Basic Science and Current Status; Georg, G., Chen, T., Ojima, I., Vyas, D., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC, 1995. For total syntheses of Taxol, see: (c) Holton, R. A.; Somoza, C.; Kim, H. B.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1597-1598, 1599-1600. (d) Nicolaou, K. C.; Yang, Z.; Ueno, H.; Nantermet, P. G.; Guy, R. K.; Claiborne, C. F.; Renaud, J.; Couladouros, E. A.; Paulvannan, K.; Sorensen, E. J. Nature 1994, 367, 630. (e) Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, J. J. Am. Chem. Soc. 1996, 118, 2843-2859 and references cited therein.
5. Taxol is the registered trademark for the molecule with generic name paclitaxel. For a recent review of synthetic studies from over 35 groups, see: (a) Wender, P. A.; Natchus, M. G.; Shuker, A. J. In TAXOL® Science and Applications; Suffness, M., Ed.; CRC Press: New York, 1995; pp 123-187. For overviews of other aspects of taxol research, see: (b) Taxane Anticancer Agents: Basic Science and Current Status; Georg, G., Chen, T., Ojima, I., Vyas, D., Eds.; ACS Symposium Series 583; American Chemical Society: Washington, DC, 1995. For total syntheses of Taxol, see: (c) Holton, R. A.; Somoza, C.; Kim, H. B.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1597-1598, 1599-1600. (d) Nicolaou, K. C.; Yang, Z.; Ueno, H.; Nantermet, P. G.; Guy, R. K.; Claiborne, C. F.; Renaud, J.; Couladouros, E. A.; Paulvannan, K.; Sorensen, E. J. Nature 1994, 367, 630. (e) Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, J. J. Am. Chem. Soc. 1996, 118, 2843-2859 and references cited therein.
6. Wender, P. A.; Mucciaro, T. P. J. Am. Chem. Soc. 1992, 114, 5878-5879. For a recently reported attractive application of this strategy, see: Winkler, J. D.; Bhattacharya, S. K.; Liotta, F.; Batey, R. A.; Hefferman, G. D.; Cladingboel, D. E.; Kelly, R. C. Tetrahedron Lett. 1995, 36, 2211-2214.
7. Wender, P. A.; Mucciaro, T. P. J. Am. Chem. Soc. 1992, 114, 5878-5879. For a recently reported attractive application of this strategy, see: Winkler, J. D.; Bhattacharya, S. K.; Liotta, F.; Batey, R. A.; Hefferman, G. D.; Cladingboel, D. E.; Kelly, R. C. Tetrahedron Lett. 1995, 36, 2211-2214.
8. Presented in part at the ACS Western Regional Meeting, Oct 18-21, 1995, ORGN. 129. For an overview of our strategy see: Wender, P. A.; Badham, N. F.; Conway, S. P.; Floreancig, P. E.; Glass, T. E.; Houze, J. B.; Krauss, N. E.; Lee, D.; Marquess, D. G.; McGrane, P. L.; Meng, W.; Mucciaro, T. P.; Mühlebach, M.; Natchus, M. G.; Ohkuma, T.; Peschke, B.; Rawlins, D. B.; Shuker, A. J.; Sutton, J. C.; Taylor, R. E.; Tomooka, K.; Wessjohann, L. A. In ref 2b, pp 326-339.
9. Presented in part at the ACS Western Regional Meeting, Oct 18-21, 1995, ORGN. 129. For an overview of our strategy see: Wender, P. A.; Badham, N. F.; Conway, S. P.; Floreancig, P. E.; Glass, T. E.; Houze, J. B.; Krauss, N. E.; Lee, D.; Marquess, D. G.; McGrane, P. L.; Meng, W.; Mucciaro, T. P.; Mühlebach, M.; Natchus, M. G.; Ohkuma, T.; Peschke, B.; Rawlins, D. B.; Shuker, A. J.; Sutton, J. C.; Taylor, R. E.; Tomooka, K.; Wessjohann, L. A. In ref 2b, pp 326-339.
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17. The stereochemistry of the cyclopropane was confirmed by NOE experiments. Irradiating the C3 proton gave a 3% enhancement of one of the cyclopropane hydrogens and a 7% enhancement of one of the geminal methyls.
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