Total Synthesis of 12-epi-PGF2α

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 779-782

  Hwang, Seong Woo ^a   Adiyaman, Mustafa ^a   Khanapure, Subhash P ^a   Rokach, Joshua ^a  

^a Florida Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PROSTAGLANDIN F2 ALPHA;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030070784     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02390-9     Document Type: Article

References (24)

1. a) Morrow, J. D.; Harris, T. M.; Roberts II, L. J. Anal. Biochem. 1990, 184, 1.
2. b) Morrow, J. D.; Hill, K. E.; Burk, R. F.; Nammour, T. M.; Badr, K. F.; Roberts II, L. J. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 9383.
3. Morrow, J. D.; Awad, J. A.; Boss, H. J.; Blair, I. A.; Roberts II, L. J. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 10721.
4. Takahashi, K.; Nammour, T. M.; Fukunaga, M.; Ebert, J.; Morrow, J. D.; Roberts II, L. J.; Hoover, R. L.; Badr, K. F. J. Clin. Invest. 1992, 90, 136.
5. 10- positions in addition to the one shown in Scheme 1. These radicals can lead to different types of isoprostanes (ref No. 6)
6. a) Porter, N. A.; Funk, M. O. J. Org. Chem. 1975, 40, 3614.
7. b) O'Connor, D. E.; Mihelich, E. D.; Coleman, M. C. J. Am. Chem. Soc. 1984, 106, 3577.
8. c) Corey, E. J.; Shih, C.; Shih, N-Y.; Shimoji, K. Tetrahedron Lett. 1984, 25, 5013.
9. d) RajanBabu, T. V.; Fukunaga, T.; Reddy, G. S. J. Am. Chem. Soc. 1989, 111, 1759.
10. e) Curran, D. P.; Chang, C-T. J. Org. Chem. 1989, 54, 3140.
11. f) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296.
12. g) Beckwith, A. L. J.; Cliff, M. D.; Schiesser, C. H. Tetrahedron 1992, 48, 4641.
13. h) Ziegler, F. E.; Zheng, Z-I. Tetrahedron Lett. 1987, 25, 5973.
14. i) Mulzer, J.; Kermanchahi, A. K.; Buschmann, J.; Luger, P. Liebigs Ann. Chem. 1994, 531.
15. Hwang, S. W.; Adiyaman, M.; Khanapure, S.; Schio, L.; Rokach, J. J. Am. Chem. Soc. 1994, 116, 10829.
16. Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815.
17. 1H NMR of 16, peak due to CHO at δ 9.89 and a minor peak at δ 9.73). a) Brewster, D.; Myers, M.; Ormerod, J.; Otter, P.; Smith, A. C. B.; Spinner, M. E.; Turner, S. J. Chem. Soc., Perkin Trans. 1, 1973, 2796. b) Corey, E. J.; Wollenberg, R. H. J. Org. Chem. 1975, 40, 2265. c) Chen, L-Y.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1181.
18. 1H NMR of 16, peak due to CHO at δ 9.89 and a minor peak at δ 9.73). a) Brewster, D.; Myers, M.; Ormerod, J.; Otter, P.; Smith, A. C. B.; Spinner, M. E.; Turner, S. J. Chem. Soc., Perkin Trans. 1, 1973, 2796. b) Corey, E. J.; Wollenberg, R. H. J. Org. Chem. 1975, 40, 2265. c) Chen, L-Y.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1181.
19. 1H NMR of 16, peak due to CHO at δ 9.89 and a minor peak at δ 9.73). a) Brewster, D.; Myers, M.; Ormerod, J.; Otter, P.; Smith, A. C. B.; Spinner, M. E.; Turner, S. J. Chem. Soc., Perkin Trans. 1, 1973, 2796. b) Corey, E. J.; Wollenberg, R. H. J. Org. Chem. 1975, 40, 2265. c) Chen, L-Y.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1181.
20. The lactols 22 are unstable, exposure to silica gel or even storage at -20°C overnight resulted in extensive decomposition.
21. +.
22. a) Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1, 1975, 1574.
23. b) Barton, D. H. R.; Crich, D.; Lobberding, A.; Zard, S. Z. Tetrahedron 1986, 42, 2329.
24. Williams, D. R.; Moore, J. L. Tetrahedron Lett. 1983, 24, 339.