Total synthesis of (±)-taxusin

Journal of the American Chemical Society

Volumn 118, Issue 38, 1996, Pages 9186-9187

  Hara, Ryoma ^a   Furukawa, Takashi ^a   Horiguchi, Yoshiaki ^a   Kuwajima, Isao ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

TAXANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029824092     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9610949     Document Type: Article

References (31)

1. There have been reported four total syntheses of natural taxanes. For taxusin, see: (a) Holton, R. A.; Juo, R. R.; Kim, H.-B.; Williams, A. D.; Harusawa, S.; Lowenthal, R. E.; Yogai, S. J. Am. Chem. Soc. 1988, 110, 6558. For taxol, see: (b) 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, 1599. (c) Nicolaou, K. C.; Yang, Z.; Liu, J. J.; 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. Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Sorensen, E. J. J. Am. Chem. Soc. 1995, 117, 624 and following papers. (d) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1723.
2. There have been reported four total syntheses of natural taxanes. For taxusin, see: (a) Holton, R. A.; Juo, R. R.; Kim, H.-B.; Williams, A. D.; Harusawa, S.; Lowenthal, R. E.; Yogai, S. J. Am. Chem. Soc. 1988, 110, 6558. For taxol, see: (b) 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, 1599. (c) Nicolaou, K. C.; Yang, Z.; Liu, J. J.; 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. Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Sorensen, E. J. J. Am. Chem. Soc. 1995, 117, 624 and following papers. (d) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1723.
3. There have been reported four total syntheses of natural taxanes. For taxusin, see: (a) Holton, R. A.; Juo, R. R.; Kim, H.-B.; Williams, A. D.; Harusawa, S.; Lowenthal, R. E.; Yogai, S. J. Am. Chem. Soc. 1988, 110, 6558. For taxol, see: (b) 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, 1599. (c) Nicolaou, K. C.; Yang, Z.; Liu, J. J.; 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. Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Sorensen, E. J. J. Am. Chem. Soc. 1995, 117, 624 and following papers. (d) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1723.
4. There have been reported four total syntheses of natural taxanes. For taxusin, see: (a) Holton, R. A.; Juo, R. R.; Kim, H.-B.; Williams, A. D.; Harusawa, S.; Lowenthal, R. E.; Yogai, S. J. Am. Chem. Soc. 1988, 110, 6558. For taxol, see: (b) 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, 1599. (c) Nicolaou, K. C.; Yang, Z.; Liu, J. J.; 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. Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Sorensen, E. J. J. Am. Chem. Soc. 1995, 117, 624 and following papers. (d) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1723.
5. There have been reported four total syntheses of natural taxanes. For taxusin, see: (a) Holton, R. A.; Juo, R. R.; Kim, H.-B.; Williams, A. D.; Harusawa, S.; Lowenthal, R. E.; Yogai, S. J. Am. Chem. Soc. 1988, 110, 6558. For taxol, see: (b) 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, 1599. (c) Nicolaou, K. C.; Yang, Z.; Liu, J. J.; 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. Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Sorensen, E. J. J. Am. Chem. Soc. 1995, 117, 624 and following papers. (d) Masters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1723.
6. For reviews, see: (a) Georg, G. I.; Chen, T. T.; Ojima, I.; Vyas, D. M. Taxane Anticancer Agents; American Cancer Society: San Diego, CA, 1995. (b) Kingston, D. G. I.; Molinero, A. A.; Rimoldo, J. M. Prog. Chem. Org. Nat. Prod. 1993, 61, 1. (c) Rowinsky, E. K.; Onetto, N.; Canetta, R. M.; Arbuck, S. G. Semin. Oncol. 1992, 19, 646.
7. For reviews, see: (a) Georg, G. I.; Chen, T. T.; Ojima, I.; Vyas, D. M. Taxane Anticancer Agents; American Cancer Society: San Diego, CA, 1995. (b) Kingston, D. G. I.; Molinero, A. A.; Rimoldo, J. M. Prog. Chem. Org. Nat. Prod. 1993, 61, 1. (c) Rowinsky, E. K.; Onetto, N.; Canetta, R. M.; Arbuck, S. G. Semin. Oncol. 1992, 19, 646.
8. For reviews, see: (a) Georg, G. I.; Chen, T. T.; Ojima, I.; Vyas, D. M. Taxane Anticancer Agents; American Cancer Society: San Diego, CA, 1995. (b) Kingston, D. G. I.; Molinero, A. A.; Rimoldo, J. M. Prog. Chem. Org. Nat. Prod. 1993, 61, 1. (c) Rowinsky, E. K.; Onetto, N.; Canetta, R. M.; Arbuck, S. G. Semin. Oncol. 1992, 19, 646.
9. Kobayashi, J.; Ogiwara, A.; Hosoyama, H.; Shigemori, H.; Yoshida, N.; Sasaki, T.; Li, Y.; Iwasaki, S.; Naito, M.; Tsuruo. T. Tetrahedron 1994, 50, 7401.
10. (a) Miyazaki, M.; Shimizu, K.; Mishima, H.; Kurabayashi, M. Chem. Pharm. Bull. 1968, 16, 546.
11. (b) Liu, C. L.; Lin, Y. C.; Lin, Y. M.; Chen, F. C. T'ai-wan K'o Hsueh 1984, 38, 119.
12. (c) Erdtman, H.; Tsuno, K. Phytochemistry 1969, 8, 931.
13. (d) Lee, C. L.; Hirose, Y. Nakatsuka Mokuzai Gakkaishi 1975, 21, 249.
14. (e) Chan, W. R.; Halsall, T. G.; Hornby, G. M.; Oxford, A. W.; Sabel, W.; Bjamer, K.; Ferguson, G.; Robertson, J. M. J. Chem. Soc., Chem. Commun. 1966, 923.
15. The taxane numbering system, as illustrated in 1, is used throughout.
16. (a) Horiguchi, Y.; Furukawa, T.; Kuwajima, I. J. Am. Chem. Soc. 1989, 111, 8277.
17. (b) Furukawa, T.; Morihira, K.; Horiguchi, Y.; Kuwajima, I. Tetrahedron 1992, 48, 6975.
18. (c) Seto, M.; Morihira, K.; Katagiri, S.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I. Chem. Lett. 1993, 133.
19. (d) Morihira, K.; Seto, M.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1993, 34, 345.
20. (f) Nakamura, T.; Waizumi, N.; Tsuruta, K.; Horiguchi, Y.; Kuwajima, I. Synlett 1994, 584.
21. (g) Seto, M.; Morihira, K.; Horiguchi, Y.; Kuwajima, I. J. Org. Chem. 1994, 59, 3165.
22. 2, CuO, and BnOH, (4) DIBAL reduction, and (5) protection with TBS group.
23. Sauleau, J.; Bouget, H.; Huet, J. C. R. Acad. Sci., Ser. C 1971, 273, 829.
24. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 399.
25. The relative stereochemistry was inferred on the analogy of a closely related compound of which stereochemistry was confirmed by the X-ray analysis of its derivative, see: Takenaka, Y.; Sakai, Y.; Ohashi, Y.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I. Anal. Sci. 1993, 883. The origin of the 1,4-asymmetric induction will be discussed in detail in the full paper.
26. Still, W. C. J. Am. Chem. Soc. 1978, 100, 1481.
27. Mitsunobu, O. Synthesis 1981, 1.
28. For angular methyl group introduction via reductive cleavage of cyclopropyl ketones, see: Dauben, W. G.; Deviny, E. J. J. Org. Chem. 1966, 31, 3794.
29. Nishimura, J.; Kawabata, N.; Furukawa, J. Tetrahedron 1969, 25, 3353.
30. Although Holton reported 70% yield for the olefination, we faced rather lower yield (53% yield on 32% conversion) as long as we examined the reaction a few times in small scale. As Holton stated, 22 is susceptible to deacetylation during the olefination reaction, see: Holton, R. B. In Strategies and Tactics in Organic Synthesis; Lindberg, T., Ed.; Academic Press, Inc.: San Diego, CA, 1991; Vol. 3, pp 165-197.
31. Furukawa, T. Ph.D. Thesis, Tokyo Institute of Technology, Tokyo, 1993.