Total synthesis of (-)-pironetin

Tetrahedron Letters

Volumn 39, Issue 45, 1998, Pages 8313-8316

  Watanabe, Hiroyuki ^a   Watanabe, Hidenori ^a   Kitahara, Takeshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; EPOXIDE; LACTONE DERIVATIVE; PIRONETIN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; EXTRACTION; FERMENTATION; PLANT GROWTH; SYNTHESIS;

EID: 0032487987     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01860-7     Document Type: Article

References (28)

1. 1) (a) Yoshida, T.; Koizumi, K.; Itazaki, H. Japan Patent Kokai 1993, 5-310726.
2. (b) Kobayashi, S.; Tsuchiya, K.; Harada, T.; Nishida, M.; Kurokawa, T.; Nakagawa, T; Shimada, N. J. Antibiot. 1994, 47, 697.
3. (c) Kobayashi, S.; Tsuchiya, K.; Kurokawa, T.; Nakagawa, T; Shimada, N. J. Antibiot. 1994, 47, 703.
4. 2) (a) Yasui, K.; Tamura, Y.; Nakatani, T.; Kawada, K.; Ohtani, M. J. Org. Chem. 1995, 60, 7567.
5. (b) Gurjar, M. K.; Henri Jr, J. T.; Bose, D. S.; Rama Rao, A. V. Tetrahedron Lett. 1996, 37, 6615.
6. (c) Gurjar, M. K.; Chakrabarti, A.; Rama Rao, A. V. Heterocycles 1997, 45, 7.
7. (d) Chida, N.; Yoshinaga, M.; Tobe, T.; Ogawa, S. Chem. Commun. 1997, 1043.
8. 3) (a) Kitahara, T.; Mori, K. Tetrahedron Lett. 1985, 26, 451.
9. (b) Kitahara, T.; Kurata, H.; Mori, K. Tetrahedron 1988, 44, 4339.
10. (c) Kitahara, T.; Kiyota, H.; Kurata, H.; Mori, K. Tetrahedron 1991, 47, 1649.
11. (d) Kitahara, T.; Akao, H.; Kiyota, H. Manuscript in preparation. Preparation of 5 is as follows. (formula presented)
12. 4) The stereochemistry of 7a, 7b, and 8 could not be determined by NMR spectroscopy, but was confirmed by X-ray analysis of crystalline diol 20a. (formula presented)
13. 5) (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
14. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
15. (c) Ireland, R. E.; Lib, L. J. Org. Chem. 1993, 58, 2899.
16. 6) Davis, F. A.; Vishwakarma, L. C.; Billmers, J. M.; Finn, J. J. Org. Chem. 1984, 49, 3241.
17. 7) Okazoe, T.; Takai, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 951.
18. 8) (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
19. (b) Honda, M.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1984, 25, 3857.
20. 9) Skrydstrap, T.; Bénéchie, M.; Khoung-Huu, F. Tetrahedron Lett. 1990, 31, 7145.
21. 10) Mori, Y.; Suzuki, M. Tetrahedron Lett. 1989, 30, 4383.
22. 2 THF -10 - No reaction 17
23. 1b
24. 13) mp 77-78 °C, lit. 78-79 °C.
25. 14) Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273.
26. 15) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
27. 16) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419.
28. 17) Intramolecular Tishchenko reduction, see: Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447.