β-Stannyl Enones as Radical Traps: A Very Direct Route to PGF

Journal of Organic Chemistry

Volumn 52, Issue 13, 1987, Pages 2958-2960

  Keck, Gary E ^a   Burnett, Duane A ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001372142     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00389a069     Document Type: Article

References (13)

1. Hart, D. J. Science (Washington, D. C.) 1984, 234, 883. (b) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: New York, 1986. (c) A recent Symposium-in-Print has been devoted to radical reactions and contains many relevant articles: Giese. B., Ed. Tetrahedron Symp. 1985. 41. 3887.
2. Keck, G. E.; Yates, J. B. J. Am. Chem. Soc. 1982, 104, 5829. (b) Keck, G. E.; Enholm, E. J.; Yates, J. B.; Wiley, M. R. Tetrahedron Symp. 1985, 41, 4079. (c) Keck, G. E.; Byers, J. H. J. Org. Chem. 1985, 50, 5442. (d) Baldwin, J. E.; Adlington, R. M.; Birch, D. J.; Crawford, J. A.; Sweeny, J. B. J. Chem. Soc., Chem. Commun. 1986, 1339.
3. Baldwin, J. E.; Adlington, R. M.; Basak, A. J. Chem. Soc., Chem. Commun. 1984, 1284.
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6. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303. (b) Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1983, 105, 6765. (c) Stork, G.; Mook, R., Jr. J. Am. Chem. Soc. 1983, 105, 3720. (d) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983,105, 3741. (e) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500. (f) Stork, G. Selectivity—A Goal for Synthetic Efficiency; Bartman, W., Trost, B. M., Eds.; Verlag Chemie: Basel, 1984; pp 281–299.
7. Stork, G.; Sher, P. M.; Chen, H. L. J. Am. Chem. Soc. 1986, 108, 6384.
8. Noyori, R.; Tomino, I.; Nichizawa, M. J. Am. Chem. Soc. 1979, 101, 5843. (b) Noyori, R.; Tomino, I.; Tanimoto, Y.; Nichizawa, M. J. Am. Chem. Soc. 1984, 106, 6709. (c) Noyori, R.; Tomino, I.; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717.
9. Corey, E. J.; Weinshenker, N. M.; Schaaf, T. K.; Huber, W. J. Am. Chem. Soc. 1969. 91. 5675.
10. Kaneko, C.; Sugimoto, A.; Tanaka, S. Synthesis 1974, 876. (b) All compounds described herein are derived from 5a and are racemic, although only one enantiomer is shown for convenience. The Stork route8 employs the (-)-monoacetate of 5a (which is available by enzyme-catalyzed hydrolysis of the diacetate of 5a) for conversion to natural (+)-Pgf2q.
11. Corey, E. J.: Vankateswarlu. A. J. Am. Chem. Soc. 1972, 90, 6190.
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13. Overberger, C. G.; Biletch, H.; Finestone, A. B.; Lilker, J.; Herbert, J. J. Am. Chem. Soc. 1953, 75, 2078 and references therein. (b) For a discussion of “some properties of radical reactions important in synthesis”, note: Walling, C. Tetrahedron Symp. 1985, 41, 3887.