Carbonylation of epoxides to substituted 3-hydroxy-α-lactones

Organic Letters

Volumn 9, Issue 26, 2007, Pages 5581-5583

  Kramer, John W ^a   Joh, Daniel Y ^a   Coates, Geoffrey W ^a  

^a Department of Molecular Biology and Genetics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; KETONE; LACTONE;

ARTICLE; CHEMISTRY; INFRARED SPECTROPHOTOMETRY;

EPOXY COMPOUNDS; KETONES; LACTONES; SPECTROPHOTOMETRY, INFRARED;

EID: 38349090243     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702475e     Document Type: Article

References (28)

1. Aggarwal, V. K.; Bae, I.; Lee, H.-Y. Tetrahedron 2004, 60, 9725-9733.
2. Sharma, A.; Chattopadhyay: S. J. Org. Chem. 1999, 64, 8059-8062.
3. Cefalo, D. R.; Kiely, A. F.; Wuchrer, M.; Jamieson, J. Y.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 3139-3140.
4. Stevenson, R.; Weber, J. V. J. Nat. Prod. 1988, 51, 1215-1219.
5. (a) Tolbert, J. A. Nat. Rev. Drug Discovery 2003, 2, 517-526.
6. (b) de Lorenzo, F.; Feher, M.; Martin, J.: Collot-Teixeira, S.; Dotsenko, O.; McGregor, J. L. Curr. Med. Chem. 2006, 13, 3385-3393.
7. (a) Ranganathan, A.; Timoney, M.; Bycroft, M.; Cortés, J.; Thomas, I. P.; Wilkinson, B.; Kellenberger, L.; Hanefeld, U.; Galloway, I. S.; Staunton, J.; Leadlay, P. F. Chem. Biol. 1999, 6, 731-738.
8. (b) Greenberg, W. A.; Varvak, A.; Hanson, S. R.; Wong, K.; Huang, H.; Chen, P.; Burk, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5788-5793.
9. (a) Gijsen, H. J.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 7585-7591.
10. (b) Heine, A.; Luz, J. G.; Wong, C.-H.; Wilson, I. A. J. Mol. Biol. 2004, 343, 1019-1034.
11. (a) Loubinoux, B.; Sinnes, J.-L.; O'Sullivan, A. C.; Winkler, T. Tetrahedron 1995, 51, 3549-3558.
12. (b) Kim, S.-J.; Kang, H.-Y.; Sherman, D. H. Synthesis 2001, 1790-1793.
13. (c) Le Sann, C.; Muñoz, D. M.; Saunders, N.; Simpson, T. J.; Smith, D. I.; Soulas, F.; Watts, P.; Willis, C. L. Org. Biomol. Chem. 2005, 3, 1719-1728.
14. Reddy, M. V. R.; Brown, H. C.; Ramachandran, P. V. J. Organomet. Chem. 2001, 624, 239-243.
15. Fournier, L.; Gaudel-Siri, A.; Kocienski, P. J.; Pons, J.-M. Synlett 2003, 107-111.
16. (a) Getzler, Y. D. Y. L.; Mahadevan, V.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 1174-1175.
17. (b) Mahadevan, V.; Getzler, Y. D. Y. L.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2781-2784.
18. (c) Schmidt, J. A. R.; Mahadevan, V.; Getzler, Y. D. Y. L.; Coates, G. W. Org. Lett. 2004, 6, 373-376.
19. (d) Kramer, J. W.; Lobkovsky, E. B.; Coates, G. W. Org. Lett. 2006, 8, 3709-3712.
20. (e) Rowley, J. M.; Lobkovsky, E. B.; Coates. G. W. J. Am. Chem. Soc. 2007, 129, 4948-4960.
21. (a) Brima, T. U.S. Patent Appl. 4,968,817; Chem. Abstr., 1990, 114, 185246.
22. (b) Church, T. L.; Getzler, Y. D. Y. L.; Byrne, C. M.; Coates, G. W. Chem. Commun. 2007, 657-674.
23. Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278-280.
24. See Supporting Information.
25. 13
26. Heck, R. F. J. Am. Chem. Soc. 1963, 85, 1460-1463.
27. Church, T. L.; Getzler, Y. D. Y. L.; Coates, G. W. J. Am. Chem. Soc. 2006, 128, 10125-10133.
28. MacKeith, R. A.; McCague, R.; Olivo, H. F.; Roberts, S. M.; Taylor, S. J. C.; Xiong, H. Bioorg. Med. Chem. 1994, 2, 387-394.