An efficient synthesis of 12-epi-carbacyclins using a palladium-mediated tandem alkene insertion strategy

Bulletin of the Korean Chemical Society

Volumn 23, Issue 1, 2002, Pages 86-92

  Lee, Nam Ho ^a   Larock, Richard C ^b  

^a Jeju National University   (South Korea)

^b IOWA STATE UNIVERSITY   (United States)

Author keywords

Alkene insertion; Carbacyclin; Organic synthesis; Palladium; Prostacyclin

Indexed keywords

1 OCTEN 3 ONE; ALKENE DERIVATIVE; CARBACYCLIN DERIVATIVE; KETONE DERIVATIVE; PALLADIUM; PROSTACYCLIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ORGANIC CHEMISTRY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037138235     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2002.23.1.086     Document Type: Article

References (33)

1. Moncada, S.; Gryglewski, R. J.; Bunting, S.; Vane, J. R. Nature 1976, 263, 663.
2. Johnson, R. A.; Morton, D. R.; Kinner, J. H.; Gorman, R. R.; McGuire, J. C.; Sun, F. F.; Whittaker, N.; Bunting, S.; Salmon, J.; Moncada, S.; Vane, J. R. Prostaglandins 1976, 12, 915.
3. For recent papers related to synthesis of prostacyclin analogues, see: (a) Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533. (b) Matsumura, Y.; Shimada, T.; Nakayama, T.; Urushihara, M.; Asai, T.; Morizawa, Y.; Yasuda, Y. Tetrahedron 1995, 51, 8771. (c) Node, M.; Inoue, T.; Araki, M.; Nakamura, D. Tetrahedron: Asymmetry 1998, 9, 157. (d) Negishi, E. I.; Pour, M.; Cederbaum, F. E.; Kotora, M. Tetrahedron 1998, 54, 7057.
4. For recent papers related to synthesis of prostacyclin analogues, see: (a) Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533. (b) Matsumura, Y.; Shimada, T.; Nakayama, T.; Urushihara, M.; Asai, T.; Morizawa, Y.; Yasuda, Y. Tetrahedron 1995, 51, 8771. (c) Node, M.; Inoue, T.; Araki, M.; Nakamura, D. Tetrahedron: Asymmetry 1998, 9, 157. (d) Negishi, E. I.; Pour, M.; Cederbaum, F. E.; Kotora, M. Tetrahedron 1998, 54, 7057.
5. For recent papers related to synthesis of prostacyclin analogues, see: (a) Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533. (b) Matsumura, Y.; Shimada, T.; Nakayama, T.; Urushihara, M.; Asai, T.; Morizawa, Y.; Yasuda, Y. Tetrahedron 1995, 51, 8771. (c) Node, M.; Inoue, T.; Araki, M.; Nakamura, D. Tetrahedron: Asymmetry 1998, 9, 157. (d) Negishi, E. I.; Pour, M.; Cederbaum, F. E.; Kotora, M. Tetrahedron 1998, 54, 7057.
6. For recent papers related to synthesis of prostacyclin analogues, see: (a) Collins, P. W.; Djuric, S. W. Chem. Rev. 1993, 93, 1533. (b) Matsumura, Y.; Shimada, T.; Nakayama, T.; Urushihara, M.; Asai, T.; Morizawa, Y.; Yasuda, Y. Tetrahedron 1995, 51, 8771. (c) Node, M.; Inoue, T.; Araki, M.; Nakamura, D. Tetrahedron: Asymmetry 1998, 9, 157. (d) Negishi, E. I.; Pour, M.; Cederbaum, F. E.; Kotora, M. Tetrahedron 1998, 54, 7057.
7. (a) Nicolaou, K. C.; Sipio, W. J.; Magolda, R. L.; Seits, S.; Barnett, W. E. J. Chem. Soc., Chem. Commun. 1978, 1067.
8. (b) Kojima, K.; Sakai, K. Tetrahedron Lett. 1978, 3743.
9. (c) Shibasaki, M.; Ueda, J.; Ikegami, S. Tetrahedron Lett. 1979, 433.
10. (d) Morton Jr., D. R.; Brokaw, F. C. J. Org. Chem. 1979, 44, 2880.
11. (a) Whittle, B. J.; Moncada, S.; Whiting, F.; Vane, J. R. Prostaglandins 1980, 19, 605.
12. (b) Aiken, J. W.; Shebuski, R. J. Prostaglandins 1980, 19, 629.
13. (c) Whittle, B. J. R.; Steel, G.; Boughton-Smith, N. K. J. Pharm. Pharmacol. 1980, 32, 603.
14. (a) Skuballa, W.; Vorbruggen, H. Angew. Chem., Int. Ed. Engl. 1981, 20, 1046.
15. (b) Stock, G.; Muller, B.; Krais, T.; Schillinger, E. Adv. Prostaglandin, Thromboxane, Leukotriene Res. 1990, 10, 285.
16. (a) Larock, R. C.; Lee, N. H. J. Am. Chem. Soc. 1991, 113, 7815.
17. (b) Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253.
18. (c) Lee, N. H.; Larock, R. C. Bull. Korean Chem. Soc. 1995, 16, 859.
19. This results have been published as a communication, see: Larock, R. C.; Lee, N. H. Tetrahedron Lett. 1991, 32, 5911.
20. (a) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494.
21. (b) Ito, Y.; Aoyama, H.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 4519.
22. (c) Kende, A. S.; Roth, B.; Sanfilippo, P. J. J. Am. Chem. Soc. 1982, 104, 1784.
23. (d) Kende, A. S.; Roth, B.; Sanfilippo, P. J.; Black, T. J. J. Am. Chem. Soc. 1982, 104, 5808.
24. (a) Trost, B. M.; Molander, G. M. J. Am. Chem. Soc. 1981, 103, 5969.
25. (b) Deardorff, D. R.; Myles, D. C.; Macferrin, K. D. Tetrahedron Lett. 1985, 26, 5615.
26. Krapcho, A. P. Synthesis 1982, 893.
27. Fleming, I.; Paterson, L. Synthesis 1979, 736.
28. For a study on the chemoselective, but not stereoselective, enone reduction at C-15 in PGs in the presence of a saturated ketone, see: Green, A. E.; Teixeira, M. A.; Barreiro, E.; Cruz, A.; Crabbe, P. J. J. Org. Chem. 1982, 47, 2553.
29. (a) Noyori, R.; Tomio, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709.
30. (b) Noyori, R.; Tomio, I.; Yamada, M.; Nishizawa. M. J. Am. Chem. Soc. 1984, 106, 6717.
31. (a) Sugie, A.; Shimomura, H.; Katsube, J.; Yamamoto, H. Tetrahedron Lett. 1979, 2067.
32. (b) Newton, R. F.; Wadsworth, A. J. Chem. Soc., Perkin Trans. I 1982, 823.
33. (c) Skuballa, W. Tetrahedron Lett. 1980, 21, 3261.