Enantioselective synthesis of the tricyclic core of GKK1032, novel antibiotic anti-tumor agents, by employing an intramolecular Diels-Alder cycloaddition strategy

Synlett

Volumn , Issue 10, 2005, Pages 1539-1542

  Asano, Moriteru ^a   Inoue, Munenori ^a,b   Katoh, Tadashi ^c  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^c TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Anti tumor agents; Antimicrobial agents; Diels Alder reaction; GKK1032s; Natural product synthesis; Stille coupling

Indexed keywords

ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; GKK 1032;

ARTICLE; CYCLOADDITION; DIELS ALDER REACTION; DRUG SYNTHESIS; ENANTIOSELECTIVITY;

EID: 21544473193     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-869843     Document Type: Article

References (29)

1. (a) Koizumi, F.; Hasegawa, A.; Ando, K.; Ogawa, T.; Hara, M. Jpn. Kokai Tokyo Koho; JP 2001247574, 2001.
2. (b) Hasegawa, A.; Koizutni, F.; Takahashi, Y.; Ando, K.; Ogawa, T.; Hara, M.; Yoshida, M. 43rd Tennen Yuki Kagobutu Touronnkai Koen Yoshishu; Osaka Japan, 2001, 467.
3. Omura, S.; Komiyama, K.; Hayashi, M.; Masuma, R.; Fukami, A Jpn. Kokai Tokkyo Koho; JP 2002255969, 2002.
4. He, H.; Yang, H. Y.; Bigelis, R.; Solum, E. H.; Greenstein, M.; Carter, G. T. Tetrahedron Lett. 2002, 43, 1633.
5. Oikawa, H. J. Org. Chem. 2003, 68, 3552.
6. Quite recently, three other synthetic studies of GKK1032s and pyrrocidines were independently presented by Kuwajima's group, Tadano's group, and Uchiro's group: (a) Arai, N.; Kuwajima, I. The 85th Annual Spring Meeting of the Chemical Society of Japan, Yokohama Japan 2005, Abstract 2, 872.
7. (b) Kurosaka, J.; Sinkawa, T.; Miyazaki, Y.; Munakata, R.; Takao, K.; Tadano, K. The 85th Annual Spring Meeting of the Chemical Society of Japan, Yokohama Japan 2005, Abstract 2, 874.
8. (c) Hasegawa, D.; Sakuma, Y.; Takagi, Y.; Uchiro, T. The 125th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo Japan 2005, Abstract 4, 71.
9. (a) Danishefsky. S.; Kitahara, T. J. Am. Chem. Soc. 1974, 96. 7807.
10. (b) Danishefsky, S.; Kitahara, T.; Schuda, P. F. Org. Synth., Coll. Vol. 7 1990, 312.
11. (a) Izquierdo Cubero, I.; Portal Olea, M. D.; Garcia Poza, D. Carbohydr. Res. 1985, 138, 135.
12. (b) Schmid, C. R.; Bryant, J. D.; Dowlatzedah, M.; Phillips, J. L.; Prather, D. E.; Schantz, R. D.; Sear, N. L.; Vianco, C. S. J. Org. Chem. 1991, 56, 4056.
13. +]: 253.1440; found: 253.1448.
14. Ortuño, R. M.; Ibarzo, J.; d'Angelo, J.; Dumas, F.; Alvarez-Larena, A.; Piniella, J. F. Tetrahedron: Asymmetry 1996, 7, 127.
15. Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 14, 4607.
16. (a) Corey, E. J.; Wollenberg, R. H. J. Am. Chem., Soc. 1974, 96, 5581.
17. (b) Chen, S.-M. L.; Schaub, R. E.; Grudzinskas, C. V. J. Org. Chem. 1978, 43, 3450.
18. (a) Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468.
19. (b) Smith, N.D.; Mancuso, J.; Lautens, M. Chem. Rev. 2000, 100, 3257.
20. Hart, D. W.; Blackburn, T. F.; Schwartz, J. J. Am. Chem. Soc. 1975, 97, 679.
21. Semmelhack, M. F.; Hooley, R. J. Tetrahedron Lett. 2003, 44, 5737.
22. Gómez, A. M.; Lopez, J. C.; Fraser-Reid, B. Synthesis 1993, 943.
23. Han, X.; Stoltz, B. M.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 7600.
24. Detailed discussions on this IMDA reaction will be presented in a full account.
25. The vinylstannane 9 was prepared from the known compound i: (a) Scarlato, G. R.; DeMattei, J. A.; Chong, L. S.; Ogawa, A. K.; Lin, M. R.; Armstrong, R. W. J. Org. Chem. 1996, 61, 6139.
26. (b) Baker, R.; Castro, J. L. J. Chem. Soc., Perkin Trans, 1 1990, 47; via a two-step sequence of reactions as shown in Scheme 6. (Diagram presented)
27. +): 422.1949; found: 422.1954.
28. +): 422.1949; found 422.1950.
29. In this IMDA reaction, a small amount (<10% yield) of unidentified products was generated along with the desired decahydrofluorene 6.