Efficient synthesis of thiopyrans using a sulfur-enabled anionic cascade

Angewandte Chemie - International Edition

Volumn 51, Issue 8, 2012, Pages 1938-1941

  Li, Fang ^a   Calabrese, David ^b   Brichacek, Matthew ^b   Lin, Ivy ^a   Njardarson, Jon T ^a  

^a University of Arizona   (United States)

^b Baker Laboratory ^*  (United States)

Author keywords

carbocycles; cyclizations; steroids; sulfur heterocycles; synthetic methods

Indexed keywords

CARBOCYCLES; CYCLIZATIONS; STEROIDS; SULFUR HETEROCYCLES; SYNTHETIC METHODS;

KETONES; ORGANIC COMPOUNDS;

SULFUR;

EID: 84856833473     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201108261     Document Type: Article

References (27)

1. E. Schaumann, Top. Curr. Chem. 2007, 274, 1-34.
2. N. A. McGrath, M. Brichacek, J. T. Njardarson, J. Chem. Educ. 2010, 87, 1348-1349.
3. E. Rogers, H. Araki, L. A. Batory, C. E. McInnis, J. T. Njardarson, J. Am. Chem. Soc. 2007, 129, 2768-2769.
4. For an example of a recently programmed anionic cascade, see:, A. B. Smith III, M. Xian, J. Am. Chem. Soc. 2006, 128, 66-67.
5. E. Vedejs, G. A. Krafft, Tetrahedron 1982, 38, 2857-2881.
6. C. R. Johnson, K. Tanaka, Synthesis 1976, 413-414
7. P. Beak, P. D. Becker, J. Org. Chem. 1982, 47, 3855-3861.
8. A. I. Meyers, M. E. Ford, Tetrahedron Lett. 1975, 16, 2861-2864.
9. I. Macia̧giewicz, P. Dybowski, A. Skowroñska, Tetrahedron Lett. 1999, 40, 3791-3794.
10. These five β-thiophosphate esters (Table 3, 8 a-e) were obtained from conjugate addition of diethylphosphorodithioate to the corresponding enoates., B. C. Ranu, S. S. Dey, Tetrahedron 2004, 60, 4183-4188.
11. H.-J. Liu, K.-S. Shia, X. Shang, B.-Y. Zhu, Tetrahedron 1999, 55, 3803-3830.
12. R. Betík, M. Kotora, Eur. J. Org. Chem. 2011, 3279-3282.
13. This type of thiosteroidal architecture is a rare construct., T. Terasawa, T. Okada, J. Org. Chem. 1981, 46, 381-386.
14. K. Kondo, A. Negishi, K. Matsui, D. Tunemoto, J. Chem. Soc. Chem. Commun. 1972, 1311-1312
15. P. L. Stotter, R. E. Hornish, J. Am. Chem. Soc. 1973, 95, 4444-4446.
16. L. A. Paquette, Org. React. 1977, 2, 1-71
17. R. J. K. Taylor, Chem. Commun. 1999, 217-227; for a recent thiopyran application of the Ramberg-Backlund reaction, see
18. B. M. Trost, B. M. Z. Shi, J. Am. Chem. Soc. 1994, 116, 7459-7460.
19. W. N. Speckamp, J. G. Westra, H. O. Huisman, Tetrahedron 1970, 26, 2353-2363.
20. E. Vedejs, T. H. Eberlein, D. J. Mazur, C. K. McClure, D. A. Perry, R. Ruggeri, E. Schwartz, J. S. Stultz, D. L. Varie, R. G. Wilde, S. Wittenberger, J. Org. Chem. 1986, 51, 1556-1562
21. E. Vedejs, T. H. Eberlein, R. G. Wilde, J. Org. Chem. 1988, 53, 2220-2226.
22. J. M. McIntosh, H. Khalil, Can. J. Chem. 1976, 54, 1923-1928
23. M. Barreau, G. Ponsinet, Tetrahedron Lett. 1985, 26, 5451-5452.
24. Y.-S. Shon, T. R. Lee, Tetrahedron Lett. 1997, 38, 1283-1286
25. G. Spagnol, M.-P. Heck, S. P. Nolan, C. Mioskowski, Org. Lett. 2002, 4, 1767-1770.
26. M. Reglier, S. A. Julia, Tetrahedron Lett. 1985, 26, 2319-2322
27. A. P. Dobbs, S. J. J. Guesne, S. Martinovic, S. J. Coles, M. B. Hursthouse, J. Org. Chem. 2003, 68, 7880-7883.