A → J prostaglandin swap: A new tactic for cyclopentenone prostaglandin synthesis

Journal of Organic Chemistry

Volumn 68, Issue 17, 2003, Pages 6803-6805

  Zanoni, Giuseppe ^a   Castronovo, Francesca ^a   Perani, Eleonora ^a   Vidari, Giovanni ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

OPTIMIZATION; SELENIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

PROSTAGLANDINS;

KETONES;

CYCLOPENTENONE DERIVATIVE; HYDROXYL GROUP; PROSTAGLANDIN A2; PROSTAGLANDIN J2; SELENIUM; 9-DEOXY-DELTA-9-PROSTAGLANDIN D2; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PROSTAGLANDIN; PROSTAGLANDIN A; PROSTAGLANDIN D2;

ANTIINFLAMMATORY ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PROSTAGLANDIN SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

INDICATORS AND REAGENTS; MODELS, MOLECULAR; PROSTAGLANDIN D2; PROSTAGLANDINS; PROSTAGLANDINS A;

EID: 2142821345     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034501p     Document Type: Article

References (21)

1. Neghishi, M.; Katoh, H. Prostaglandins Lipid Mediators 2002, 68-69, 611-617 and references therein.
2. Straus, D. S.; Glass, C. K. Med. Res. Rev. 2001, 21, 185-210 and references therein.
3. Rossi, A.; Elia, G.; Santoro, M. G. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 746-750.
4. (a) Forman, B. M.; Tontonoz, P.; Brun, R. P.; Spiegelman, B. M.; Evans, R. M. Cell 1995, 83, 803-812.
5. (b) Kliewer, S. A.; Lenhard, J. M.; Willson, T. M.; Patel, I.; Lehmann, J. M. Cell 1995, 83, 813-819.
6. To date only a limited number of total syntheses have been reported in the literature: (a) Ali, S. M.; Chapleo, B. C.; Finch, M. A. W.; Roberts, S. M. ; Wooley, G. T.; Cave, R. C.; Newton, R. F. J. Chem. Soc., Perkin Trans. 1 1980, 2093-2097. (b) Bundy, G. L.; Morton, D. R.; Peterson, D. C.; Nishizawa, E. E.; Miller, W. L. J. Med. Chem. 1983, 6, 790-799. (c) Ali, M. S.; Finch, M. A. W.; Roberts, S. M.; Newton, R. F. J. Chem. Soc., Chem. Commun. 1979, 679-682.
7. To date only a limited number of total syntheses have been reported in the literature: (a) Ali, S. M.; Chapleo, B. C.; Finch, M. A. W.; Roberts, S. M. ; Wooley, G. T.; Cave, R. C.; Newton, R. F. J. Chem. Soc., Perkin Trans. 1 1980, 2093-2097. (b) Bundy, G. L.; Morton, D. R.; Peterson, D. C.; Nishizawa, E. E.; Miller, W. L. J. Med. Chem. 1983, 6, 790-799. (c) Ali, M. S.; Finch, M. A. W.; Roberts, S. M.; Newton, R. F. J. Chem. Soc., Chem. Commun. 1979, 679-682.
8. To date only a limited number of total syntheses have been reported in the literature: (a) Ali, S. M.; Chapleo, B. C.; Finch, M. A. W.; Roberts, S. M. ; Wooley, G. T.; Cave, R. C.; Newton, R. F. J. Chem. Soc., Perkin Trans. 1 1980, 2093-2097. (b) Bundy, G. L.; Morton, D. R.; Peterson, D. C.; Nishizawa, E. E.; Miller, W. L. J. Med. Chem. 1983, 6, 790-799. (c) Ali, M. S.; Finch, M. A. W.; Roberts, S. M.; Newton, R. F. J. Chem. Soc., Chem. Commun. 1979, 679-682.
9. (a) Krafft, M. E.; Wright, C. Tetrahedron Lett. 1992, 33, 151-152 and references therein.
10. ApSimon, J. The Synthesis of Prostaglandins; Vol. 4, The Total Synthesis of Natural Product; Bindra, J. S., Ed.; Wiley-Interscience Publication: New York, 1981; pp 353-449.
11. 2O, 0°C, 88%
12. (b) Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298-5300.
13. Liu, Z.; Lan, J.; Li, Y. Tetrahedron: Asymmetry 1998, 9, 3755-3762.
14. Discordia, R. P.; Murphy, C. K.; Dittmer, D. C. Tetrahedron Lett. 1990, 31, 5603-5606.
15. Nemoto, H.; Matsuhashi, N.; Satoh, A.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1992, 495-498.
16. (a) Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1972, 94, 7154-7155.
17. (b) Zoretic, P. A.; Chambers, R. J.; Marbury, G. D.; Riebiro, A. A. J. Org. Chem. 1985, 50, 2981.
18. (c) For some application of [2,3] sigmatropic rearrangement of allylic selenoxide see: Back, T. G.; McPhee, D. J. J. Org. Chem. 1984, 49, 3842-3843. Koprowski, M.; Krawczyk, E.; Skowroñska, A.; McPartlin, M.; Choi, N.; Radojievic, S. Tetrahedron 2001, 57, 1105-1118.
19. (c) For some application of [2,3] sigmatropic rearrangement of allylic selenoxide see: Back, T. G.; McPhee, D. J. J. Org. Chem. 1984, 49, 3842-3843. Koprowski, M.; Krawczyk, E.; Skowroñska, A.; McPartlin, M.; Choi, N.; Radojievic, S. Tetrahedron 2001, 57, 1105-1118
20. Grieco, P. A.; Gilman, M.; Nishizawa, M. J. Org. Chem. 1976, 41, 1485-1486.
21. Chapleo, B. C.; Finch, M. A. W.; Roberts, S. M.; Lee. T. V. J. Chem. Soc., Perkin Trans. 1 1980, 2084-2087.