Total synthesis of (-)-PA-48153C (pironetin) utilising L-quebrachitol as a chiral building block

Chemical Communications

Volumn , Issue 11, 1997, Pages 1043-1044

  Chida, Noritaka ^a   Yoshinaga, Mitsukane ^a   Tobe, Takahiko ^a   Ogawa, Seiichiro ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRONE DERIVATIVE; IMMUNOSUPPRESSIVE AGENT; MALIC ACID; PIRONETIN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0030973222     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a701404j     Document Type: Article

References (26)

1. T. Yoshida, K. Koizumi, Y. Kawamura, K. Matsumoto and H. Itazaki, Jpn. Pat. Kokai, 1993, 5-310 726; Eur. Pat., 1993, 560 389 A1.
2. (a) S. Kobayashi, K. Tsuchiya, T. Harada, M. Nishide, T. Kurokawa, T. Nakagawa, N. Shimada and K. Kobayashi, J. Antibiot., 1994, 47, 697:
3. (b) S. Kobayashi, K. Tsuchiya, T. Kurokawa, T. Nakagawa, N. Shimada and Y. Iitaka, J. Antibiot., 1994, 47, 703.
4. K. Yasui, Y. Tamura, T. Nakatani, K. Kawada and M. Ohtani, J. Org. Chem., 1995, 60, 7567; M. K. Gurjar, J. T. Henri Jr. D. S. Bose and A. V. Rama Rao, Tetrahedron Lett., 1996, 37, 6615; M. K. Gurjar, A. Chakrabarti and A. V. Rama Rao, Heterocycles, 1997, 45, 7.
5. K. Yasui, Y. Tamura, T. Nakatani, K. Kawada and M. Ohtani, J. Org. Chem., 1995, 60, 7567; M. K. Gurjar, J. T. Henri Jr. D. S. Bose and A. V. Rama Rao, Tetrahedron Lett., 1996, 37, 6615; M. K. Gurjar, A. Chakrabarti and A. V. Rama Rao, Heterocycles, 1997, 45, 7.
6. K. Yasui, Y. Tamura, T. Nakatani, K. Kawada and M. Ohtani, J. Org. Chem., 1995, 60, 7567; M. K. Gurjar, J. T. Henri Jr. D. S. Bose and A. V. Rama Rao, Tetrahedron Lett., 1996, 37, 6615; M. K. Gurjar, A. Chakrabarti and A. V. Rama Rao, Heterocycles, 1997, 45, 7.
7. K. Yasui, Y. Tamura, T. Nakatani, I. Horibe, K. Kawada, K. Koizumi, R. Suzuki and M. Ohtani, J. Antibiot., 1996, 49, 173.
8. Isolation of L-quebrachitol, see; J. van Alphen, Ind. Eng. Chem., 1951, 43, 141; N. Chida, M. Suzuki, M. Suwama and S. Ogawa, J. Carbohydr. Chem., 1989, 8, 319.
9. Isolation of L-quebrachitol, see; J. van Alphen, Ind. Eng. Chem., 1951, 43, 141; N. Chida, M. Suzuki, M. Suwama and S. Ogawa, J. Carbohydr. Chem., 1989, 8, 319.
10. Utilisation of L-quebrachitol in organic synthesis, see; (a) N. Chida, K. Yamada and S. Ogawa, J. Chem. Soc., Perkin Trans. 1, 1993, 1957; (b) N. Chida and S. Ogawa, Chem. Commun., 1997, 807; J. J. Kiddle, Chem. Rev., 1995, 95, 2189.
11. Utilisation of L-quebrachitol in organic synthesis, see; (a) N. Chida, K. Yamada and S. Ogawa, J. Chem. Soc., Perkin Trans. 1, 1993, 1957; (b) N. Chida and S. Ogawa, Chem. Commun., 1997, 807; J. J. Kiddle, Chem. Rev., 1995, 95, 2189.
12. Utilisation of L-quebrachitol in organic synthesis, see; (a) N. Chida, K. Yamada and S. Ogawa, J. Chem. Soc., Perkin Trans. 1, 1993, 1957; (b) N. Chida and S. Ogawa, Chem. Commun., 1997, 807; J. J. Kiddle, Chem. Rev., 1995, 95, 2189.
13. Y. Tsuda, M. Nishimura, T. Kobayashi, Y. Sato and K. Kanemitsu, Chem. Pharm. Bull., 1991, 39, 2883; S. David and S. Hanessian, Tetrahedron, 1985, 41, 643.
14. Y. Tsuda, M. Nishimura, T. Kobayashi, Y. Sato and K. Kanemitsu, Chem. Pharm. Bull., 1991, 39, 2883; S. David and S. Hanessian, Tetrahedron, 1985, 41, 643.
15. K. Takai, K. Nitta and K. Utimoto, J. Am. Chem. Soc., 1986, 108, 7408; T. Okazoe, K. Takai and K. Utimoto, J. Am. Chem. Soc., 1987, 109, 951.
16. K. Takai, K. Nitta and K. Utimoto, J. Am. Chem. Soc., 1986, 108, 7408; T. Okazoe, K. Takai and K. Utimoto, J. Am. Chem. Soc., 1987, 109, 951.
17. L. Hughes, Org. React., 1993, 42, 656.
18. (a) M. Nakata, T. Ishiyama, S. Akamatsu, Y. Hirose, H. Maruoka, R. Suzuki and K. Tatsuta, Bull. Chem. Soc. Jpn., 1995, 68, 967;
19. (b) D. Wasmuth, D. Arigoni and D. Seebach, Helv. Chim. Acta, 1982, 65, 344.
20. Y.-S. Cheng, W.-L. Liu and S. Chen, Synthesis, 1980, 223.
21. W. C. Still and C. Gennari, Tetrahedron Lett., 1983, 24, 4405.
22. K. C. Nicolaou, K. Ajito, A. P. Patron, H. Khatuya, P. K. Richter and P. Bertinalo, J. Am. Chem. Soc., 1996, 118, 3059.
23. (a) E. J. Corey and B. W. Erickson, J. Org. Chem., 1971, 36, 3553;
24. (b) S. Shimizu, S. Nakamura, M. Nakada and M. Shibasaki, Tetrahedron, 1996, 52, 13363.
25. D. A. Evans, K. T. Chapman and E. M. Carreira, J. Am. Chem. Soc., 1988, 110, 3560; A. K. Saksena and P. Magiaracina, Tetrahedron Lett., 1983, 24, 273.
26. D. A. Evans, K. T. Chapman and E. M. Carreira, J. Am. Chem. Soc., 1988, 110, 3560; A. K. Saksena and P. Magiaracina, Tetrahedron Lett., 1983, 24, 273.