Synthesis of the key component for preparation of 6-ketoprostaglandins by a two-component coupling process: Synthesis of 6-keto-prostaglandin E1, ornoprostil and Δ2-trans-6-ketoprostaglandin E1

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 7, 1996, Pages 715-718

  Kawanaka, Yasufumi ^a   Ono, Naoya ^a   Yoshida, Yukio ^a   Okamoto, Sentaro ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0346990199     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19960000715     Document Type: Article

References (22)

1. C. P. Quilley, P. Y.-K. Wong and J. C. McGiff, European J. Pharmacol., 1979, 57, 273.
2. J. E. Lock, P. M. Olley, F. Coceani, F. Hamilton and G. Doubilet, Prostaglandins, 1979, 18, 303.
3. F. Coceani, E. Bodach, E. P. White and P. M. Olley, Prostaglandins, 1980, 19, 109.
4. H. L. Lippton, B. M. Chapnick, A. L. Hyman and P. J. Kadowiz, Prostaglandins, 1980, 19, 299.
5. Drugs Future, 1987, 12, 1023;
6. Res. Discl., 1985, 256, 400
7. (Chem. Abstr., 1986, 104, 224747c).
8. (a) M. Hayashi and K. Shimoji and Y. Arai, Japan Kokai, 1979, 54-44639;
9. (b) T. Tanaka, A. Hazato, K. Bannai, N. Okamura, S. Sugiura, K. Manabe, S. Kurozumi, M. Suzuki and R. Noyori, Tetrahedron Lett., 1984, 25, 4947;
10. T. Tanaka, A. Hazato, K. Bannai, N. Okamura, S. Sugiura, K. Manabe, T. Toru, S. Kurozumi, M. Suzuki, T. Kawagishi and R. Noyori, Tetrahedron. 1987, 43, 813.
11. (a) S. Okamato, Y. Kobayashi, H. Kato, K. Hori, T. Takahashi, J. Tsuji and F. Sato, J. Org. Chem., 1988, 53, 5590;
12. (b) S. Okamoto, N. Ono, K. Tani, Y. Yoshida and F. Sato, J. Chem. Soc., Chem. Commun., 1994, 279;
13. N. Ono, Y. Kawanaka, Y. Yoshida and F. Sato, J. Chem. Soc., Chem. Commun., 1994, 1251;
14. Y. Yoshida, Y. Sato, S. Okamoto and F. Sato, J. Chem. Soc., Chem. Commun., 1995, 811;
15. (e) Y. Yoshida, N. Ono and F. Sato, J. Org. Chem., 1994, 59, 6135 and references cited therein.
16. G. Zweifel and S. J. Backlund, J. Am. Chem. Soc., 1977, 99, 3184.
17. N. Miyaura, T. Yano and A. Suzuki, Tetrahedron Lett., 1980, 21, 2865.
18. R. K. Boeckman, Jr., and K. J. Bruza, J. Org. Chem., 1979, 44, 4781;
19. G. Stork and M. E. Jung, J. Am. Chem. Soc., 1974, 96, 3682.
20. For example, M. Hayashi, S. Koori and M. Kawamura, Japan Kokai, 1976, 51-70754.
21. C. J. Moody and P. Shah, J. Chem. Soc., Perkin Trans. 1, 1988, 3249.
22. A. Hazato, T. Tanaka, T. Toru, N. Okamura, K. Bannai, K. Sakauchi, S. Sugiura, K. Manabe and S. Kurozumi, Nippon Kagaku Kaishi, 1983, 1390.