Stereoselective total synthesis of natural (+)-streptazolin via a palladium-catalyzed enyne bicyclization approach

Journal of the American Chemical Society

Volumn 118, Issue 5, 1996, Pages 1054-1059

  Yamada, Hironari ^a   Aoyagi, Sakae ^a   Kibayashi, Chihiro ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; STREPTAZOLINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; ENANTIOMER; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0029962915     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9529910     Document Type: Article

References (29)

1. Drautz, H.; Zähner, H.; Kupfer. E.; Keller-Schierlein, W. Helv. Chim. Acta 1981, 64, 1752.
2. Grabley, S.; Hammann, P.; Kluge, H.; Wink, J.; Kricke, P.; Zeek, A. J. Antibiot. 1991, 44, 797.
3. Grabley, S.; Hammann, P.; Thiericke, R.; Wink, J.; Philipps, S.; Zeek, A. J. Antibiot. 1993, 46, 343.
4. For a biosynthetic study of streptazolin, see: Mayer, M.; Thiericke, R. J. Org. Chem. 1993, 58, 3486.
5. Karrer, A.; Dobler, M. Helv. Chim. Acta 1982, 65, 1432.
6. Wiesner, M.; Thiem, J. J. Carbohydr. Chem. 1989, 8, 705.
7. Grabley, S.; Kluge, H.; Hoppe, H.-U. Angew. Chem., Int. Ed. Engl. 1987, 26, 664.
8. Kozikowski, A. P.; Park, P. J. Am. Chem. Soc. 1985, 107, 1763. Kozikowski. A. P.; Park, P. J. Org. Chem. 1990, 55, 4668.
9. Kozikowski, A. P.; Park, P. J. Am. Chem. Soc. 1985, 107, 1763. Kozikowski. A. P.; Park, P. J. Org. Chem. 1990, 55, 4668.
10. Flann, C. J.; Overman. L. E. J. Am. Chem. Soc. 1987, 109, 6115.
11. For a review of the effective metal-organic approach to stereoselective synthesis of exocyclic alkenes, see: Negishi, E. In Advances in Metal-Organic Chemistry; Liebeskind, L. Ed., JAI Press: Greenwich, CT. 1989; Vol. 1, pp 177-207.
12. (a) Aoyagi, S.; Wang, T-C.; Kibayashi, C. J. Am. Chem. Soc. 1992, 114, 10653.
13. (b) Aoyagi, S.; Wang, T.-C.; Kibayashi, C. J. Am. Chem. Soc. 1993, 115, 11393.
14. (c) Kibayashi, C. Pure Appl. Chem. 1994, 66, 2079.
15. (a) Takai, K.; Kimura. K.; Kuroda, T.; Hiyama, T.; Nozaki. H. Tetrahedron Lett. 1983, 24, 5281.
16. (b) Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048.
17. (c) Jin, H.; Uenishi, J.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644.
18. For a review of palladium-catalyzed cycloisomerization of enynes and related recent papers, see: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Trost, B. M.; Pedregal. C. J. Am. Chem. Soc. 1992, 114, 7292. (c) Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255. (d) Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268.
19. For a review of palladium-catalyzed cycloisomerization of enynes and related recent papers, see: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Trost, B. M.; Pedregal. C. J. Am. Chem. Soc. 1992, 114, 7292. (c) Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255. (d) Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268.
20. For a review of palladium-catalyzed cycloisomerization of enynes and related recent papers, see: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Trost, B. M.; Pedregal. C. J. Am. Chem. Soc. 1992, 114, 7292. (c) Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255. (d) Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268.
21. For a review of palladium-catalyzed cycloisomerization of enynes and related recent papers, see: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34. (b) Trost, B. M.; Pedregal. C. J. Am. Chem. Soc. 1992, 114, 7292. (c) Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255. (d) Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268.
22. (a) Overman, L. E.; Malone, T. C.; Meier, G. P. J. Am. Chem. Soc. 1983, 105, 6993.
23. (b) Flann, C.; Malone, T. C.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6097.
24. Nemoto, H.; Takamatsu, S.; Yamamoto, Y. J. Org. Chem. 1991, 56, 1321.
25. Ohwada, J.; Inouye, Y.; Kimura, M.; Kakisawa, H. Bull. Chem. Soc. Jpn. 1990, 63, 287.
26. Flann, C. J.; Malone, T. C.; Overman, L. E. Org. Synth. 1990, 68, 182.
27. Kim, S.; Ahn, K. H. J. Org. Chem. 1984, 49, 1717.
28. McFarlane, W.; Wilkinson, G. Inorg. Synth. 1966, 8, 181.
29. 2 = 5.1%, with GOF = 1.19.