Efficient protocol for ring opening of spiroketals using trifluoroacetyl trifluoromethanesulfonate (TFAT)

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3619-3622

  Seok Lee, Jong ^a   Fuchs, Philip L ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; KETONE; MESYLIC ACID DERIVATIVE; SPIRO COMPOUND; STEROID; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; ISOMERISM; REACTION ANALYSIS; RING OPENING;

KETONES; MESYLATES; SPIRO COMPOUNDS; STEROIDS;

EID: 0142074834     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035284h     Document Type: Article

References (36)

1. Cephalostatin support study no. 29. For paper no. 27, see: Li, W.; Fuchs, P. L. Org. Lett. 2003, 5, 2853.
2. Tobari, A.; Teshima, M.; Koyanagi, J.; Kawase, M.; Miyamae, H.; Yoza, K. ; Takasaki, A.; Nagamura, Y.; Saito, S. Eur. J. Med. Chem. 2000, 35, 511.
3. (a) Marker, R. E.; Wagner, R. B.; Ulshafer, P. R.; Wittbecker, E. L.; Goldsmith, D. P. J.; Ruof, C. H. J. Am. Chem. Soc. 1947, 69, 2167.
4. (b) Wall, M. E.; Eddy, C. R.; Serota, S. J. Am. Chem. Soc. 1954, 76, 2849.
5. (c) Wall, M. E.; Eddy, C. R.; Serota, S. J. Am. Chem. Soc. 1954, 76, 2850.
6. (d) Scheer, I.; Kostic, R. B.; Mosettig, E. J. Am. Chem. Soc. 1955, 77, 641.
7. (e) Ziegler, J. B.; Rosen, W. E.; Shabica, A. C. J. Am. Chem. Soc. 1955, 77, 1223.
8. (f) Wall, M. E.; Serota, S.; Eddy, C. R. J. Am. Chem. Soc. 1955, 77, 1230.
9. (g) Wall, M. E.; Walens, H. A. J. Am. Chem. Soc. 1955, 77, 5661.
10. Jeong, J. U.; Fuchs, P. L. J. Am. Chem. Soc. 1994, 116, 773.
11. (a) Marker, R. E.; Rohrmann, E. J. Am. Chem. Soc. 1939, 61, 3592.
12. (b) Marker, R. E.; Rohrmann, E. J. Am. Chem. Soc. 1940, 62, 518.
13. (c) Dauben, W. G.; Fonken, G. J. J. Am. Chem. Soc. 1954, 76, 4618.
14. (d) Cameron, A. F. B.; Evans, R. M.; Hamlet, J. C.; Hunt, J. S.; Jones, P. G.; Long, A. G. J. Chem. Soc. 1955, 2807.
15. (e) Gould, D. H.; Staeudle, H.; Hershberg, E. B. J. Am. Chem. Soc. 1952, 74, 3685.
16. (f) Danievski, A. R.; Kinowski, A. Poland Patent 119829, 1984.
17. (g) Khuyen, H. N.; Dan, N. V. Tap. Chi. Hoa. Hoc. 1976, 14, 37.
18. (h) Honda, K. L.; Rao, P. R. Res. Ind. 1970, 15, 165.
19. (i) Micovic, I. V.; Invanovic, M. D.; Piatak, D. M. Synthesis 1990, 591.
20. (j) Brown, L.; Koreeda, M. J. Org. Chem. 1984, 49, 3875.
21. (k) Tavares, R.; Randoux, T.; Braekman, J.; Daloze, D. Tetrahedron 1993, 49, 5079.
22. (l) Borah, P.; Chowdhury, P. Indian J. Chem., Section B: Org. Chem. Incl. Med. Chem. 1998, 37B, 408.
23. (m) Haeuser, H. German Patent DE 19635418, 1997.
24. (n) Chowdhury, P. K.; Bordoloi, M.; Baraua, N. C.; Sarmah, H. P.; Goswami, P. K.; Saharma, Baruah, A. P.; Mathur, R. K.; Chandra, A. U.S. Patent 5808117, 1998.
25. LaCour, T. G.; Guo, C.; Bhandaru, S.; Boyd, M. R.; Fuchs, P. L. J. Am. Chem. Soc. 1998, 120, 692.
26. (a) LaCour, T. G.; Fuchs, P. L. Tetrahedron Lett. 1999, 40, 4655.
27. (b) LaCour, T. G.; Tong, Z.; Fuchs, P. L. Org. Lett. 1999, 1, 1815.
28. (a) Forbus, T. R., Jr.; Martin, J. C. J. Org. Chem. 1979, 44, 313.
29. (b) Michalak, R. S.; Martin, J. C. J. Am. Chem. Soc. 1980, 102, 5921.
30. (c) Maas, G.; Stang, P. J. J. Org. Chem. 1981, 46, 1606.
31. (d) Taylor, S. L.; Forbus, T. R., Jr.; Martin, J. C. Org. Synth. 1986, 64, 217.
32. (e) Forbus, Jr., T. R.; Taylor, S. L.; Martin, J. C. J. Org. Chem. 1987, 52, 4156.
33. (f) Sagl, D. J.; Martin, J. C. J. Am. Chem. Soc. 1988, 110, 5827.
34. (g) Kiselyov, A. S.; Harvey, R. G. Tetrahedron Lett. 1995, 36, 4005.
35. (h) Umemoto, T.; Adachi, K.; Ishihara, S. Jpn. Kodai Tokkyo Koho 1993, 8.
36. Same reaction using 1.5-2.0 equiv of TFAT at -30 to -40°C, followed by basic workup, led to conversion, during evaporation, to cyclopentadienes 23 and 24 (75%, 23/24 = 1:3.8) along with 25% of pseudo compound 21. No hemiketal was observed.