Catalytic enantioselective synthesis of naturally occurring butenolides via hetero -allylic alkylation and ring closing metathesis

Organic Letters

Volumn 13, Issue 5, 2011, Pages 948-951

  Mao, Bin ^a   Geurts, Koen ^a   Fañanás Mastral, Martín ^a   Van Zijl, Anthoni W ^a   Fletcher, Stephen P ^a   Minnaard, Adriaan J ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BIOLOGICAL PRODUCT; BUTENOLIDE; DRUG DERIVATIVE; FURAN DERIVATIVE; GAMMA BUTYROLACTONE; NEPHROSTERANIC ACID; ROCCELLARIC ACID;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

4-BUTYROLACTONE; ALKYLATION; ALLYL COMPOUNDS; BIOLOGICAL PRODUCTS; CATALYSIS; FURANS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79952161685     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102994q     Document Type: Article

References (41)

1. For reviews, see: Bandichhor, R.; Nosse, B.; Reiser, O. Top. Curr. Chem. 2005, 243, 43
2. Kitson, R. R. A.; Millemaggi, A.; Taylor, R. J. K. Angew. Chem., Int. Ed. 2009, 48, 9426
3. For selective examples on the synthesis of optically active γ-butyrolactones, see: Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669
4. Carswell, E. L.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2006, 45, 7230
5. Ube, H.; Shimada, N.; Terada, M. Angew. Chem., Int. Ed. 2010, 49, 1858
6. Harcken, C.; Brückner, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 2750
7. Braukmüller, S.; Brückner, R. Eur. J. Org. Chem. 2006, 2110
8. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483
9. Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192
10. Trost, B. M.; Hitce, J. J. Am. Chem. Soc. 2009, 131, 4572
11. Feringa, B. L.; de Lange, B.; de Jong, J. C. J. Org. Chem. 1989, 54, 2471
12. van der Deen, H.; Cuiper, A. D.; Hof, R. P.; van Oeveren, A.; Feringa, B. L.; Kellogg, R. M. J. Am. Chem. Soc. 1996, 118, 3801
13. López, F.; van Zijl, A. W.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2006, 409
14. Geurts, K.; Fletcher, S. P.; Feringa, B. L. J. Am. Chem. Soc. 2006, 118, 3801
15. For reviews, see: Harutyunyan, S. R.; den Hartog, T.; Geurts, K.; Minnaard, A. J.; Feringa, B. L. Chem. Rev. 2008, 108, 2824
16. Alexakis, A.; Bäckvall, J. E.; Krause, N.; Pamies, O.; Dieguez, M. Chem. Rev. 2008, 108, 2796
17. Teichert, J. F.; Feringa, B. L. Angew. Chem., Int. Ed. 2010, 49, 2486
18. For reviews, see: Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18
19. Monfette, S.; Fogg, D. E. Chem. Rev. 2009, 109, 3783
20. Bassetti, M.; D'Annibale, A.; Fanfoni, A.; Minissi, F. Org. Lett. 2005, 7, 1805
21. Fujii, M.; Fukumura, M.; Hori, Y.; Akita, H.; Nakamura, K.; Toriizuka, K.; Ida, Y. Tetrahedron Lett. 2006, 17, 2292
22. Takahata, H.; Uchida, Y.; Momose, T. Tetrahedron Lett. 1994, 35, 4123
23. Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628
24. Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905
25. Nishikori, H.; Ito, K.; Katsuki, T. Tetrahedron: Asymmetry 1998, 9, 1165
26. Tsuboi, S.; Sakamoto, J.; Yamashita, H.; Sakai, T.; Utaka, M. J. Org. Chem. 1998, 63, 1102
27. For selected examples of syntheses toward (-)-nephrosteranic acid and (-)-roccellaric acid, see: Mulzer, J.; Salimi, N.; Hartl, H. Tetrahedron: Asymmetry 1993, 4, 457
28. Bella, M.; Margarita, R.; Orlando, C.; Orsini, M.; Parlanti, L.; Piancatelli, G. Tetrahedron Lett. 2000, 41, 561
29. Böhm, C.; Reiser, O. Org. Lett. 2001, 3, 1315
30. Jacobi, P.; Herradura, P. Can. J. Chem. 2001, 79, 1727
31. Sibi, M. P.; Liu, P.; Ji, J. G.; Hajra, S.; Chen, J. X. J. Org. Chem. 2002, 67, 1738
32. Barros, M. T.; Maycock, C. D.; Ventura, M. R. Org. Lett. 2003, 5, 4097
33. Chhor, R. B.; Nosse, B.; Sörgel, S.; Böhm, C.; Seitz, M.; Reiser, O. Chem.-Eur. J. 2003, 9, 260
34. Lombardo, M.; Morganti, S.; Trombini, C. J. Org. Chem. 2003, 68, 997
35. Lombardo, M.; Girotti, R.; Morganti, S.; Trombini, C. Chem. Commun. 2001, 2310
36. For some consecutive AAA-RCM reactions, see: Giacomina, F.; Riat, D.; Alexakis, A. Org. Lett. 2010, 12, 1156
37. Teichert, J. F.; Zhang, S.; van Zijl, A. W.; Slaa, J. W.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2010, 12, 4658
38. HMPA = Hexamethylphosphoramide.
39. DMPU = 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1 H)-pyrimidinone.
40. Schleth, F.; Vogler, T.; Harms, K.; Studer, A. Chem.-Eur. J. 2004, 10, 4171
41. Schleth, F.; Studer, A. Angew. Chem., Int. Ed. 2004, 43, 313