Tandem cyclopropylcarbinyl/oxiranylcarbinyl radical rearrangements: An entry into the prostaglandin B1 series

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 809-812

  Ziegler, Frederick E ^a   Petersen, Anders K ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PROSTAGLANDIN B1 DERIVATIVE; PROSTAGLANDIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030068790     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02327-5     Document Type: Article

References (20)

1. Holden, K. G.; Hwang, B.; Williams, K. R.; Weinstock, J.; Harman, M.; Weisbach, J. A. Tetrahedron Lett. 1968, 1569.
2. Kondo, K.; Umemoto, T.; Yako, K.; Tunemoto, D. Tetrahedron Lett. 1978, 3927.
3. Just, G.; Simonovitch, C.; Lincoln, F. H.; Schneider, W. P.; Axen, U.; Spero, G. B.; Pike, J. E. J. Am. Chem. Soc. 1969, 91, 5364.
4. Kondo, K.; Umemoto, T.; Takahatake, Y.; Tunemoto, D. Tetrahedron Lett. 1977, 113.
5. Taber, D. F. J. Am. Chem. Soc. 1977, 99, 3513.
6. Taber, D. F.; Hoerrner, R. S. J. Org. Chem. 1992, 57, 441.
7. Ziegler, F. E.; Petersen, A. K. J. Org. Chem. 1994, 59, 2707.
8. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
9. Boeckman, R. K., Jr.; Shair, M. D.; Vargas, J. R.; Stolz, L. A. J. Org. Chem. 1993, 58, 1295.
10. Rey, M.; Dreiding, A. S. Helv. Chim. Acta 1965, 48, 1985.
11. Rhoads, S. J.; Cockroft, R. D. J. Am. Chem. Soc. 1969, 91, 2815.
12. Ohloff, G.; Pickenhagen, W. Helv. Chim. Acta 1969, 52, 880.
13. Cooper, M. S.; Heaney, H.; Newbold, A. J.; Sanderson, W. R. Synlett 1990, 533.
14. Ziegler, F. E.; Petersen, A. K. J. Org. Chem. 1995, 60, 2666.
15. Jones, R. C. F.; Schofield, J. J. Chem. Soc., Perkin Trans. 1 1990, 375.
16. Corey, E. J.; Raju, N. Tetrahedron Lett. 1983, 24, 5571.
17. Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404.
18. Negishi, E.; Swanson, D. R.; Rousset, C. J. J. Org. Chem. 1990, 55, 5406.
19. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574.
20. 3 hybridization in the carbonyl and carbinol, respectively.