Total synthesis of (±)-cavicularin: Control of pyrone diels-alder regiochemistry using isomeric vinyl sulfones

Organic Letters

Volumn 15, Issue 2, 2013, Pages 402-405

  Zhao, Peng ^a   Beaudry, Christopher M ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAVICULARIN; DIVINYL SULFONE; ETHER DERIVATIVE; PYRONE DERIVATIVE; SULFONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ETHERS, CYCLIC; MOLECULAR STRUCTURE; PYRONES; STEREOISOMERISM; SULFONES;

EID: 84872526973     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol303390a     Document Type: Article

References (30)

1. Keseru, G. M.; Nógrádi, M. Nat. Prod. Rep. 1995, 12, 69-75
2. Asakawa, Y.; Toyota, M.; Hashimoto, T.; Tori, M.; Nagashima, F.; Harinantenaina, L. Heterocycles 2008, 76, 99-127
3. Toyota, M.; Yoshida, T.; Kan, Y.; Takaoka, S.; Asakawa, Y. Tetrahedron Lett. 1996, 37, 4745-4748
4. Salih, M. Q.; Beaudry, C. M. Org. Lett. 2012, 14, 4026-4029
5. Harrowven, D. C.; Woodcock, T.; Howes, P. D. Angew. Chem., Int. Ed. 2005, 44, 3899-3901
6. Kostiuk, S. L.; Woodcock, T.; Dudin, L. F.; Howes, P. D.; Harrowven, D. C. Chem.-Eur. J. 2011, 17, 10906-10915
7. Dam, J. H., Ph.D. Thesis, Technical University of Denmark, 2009.
8. Gulder, T.; Dam, J. H.; Baran, P. S. Abstracts of Papers, Western Regional Meeting of the American Chemical Society, Las Vegas, NV, Sept 23-27, 2008.
9. Gulder, T.; Baran, P. S. Nat. Prod. Rep. 2012, 29, 899-934
10. Baran, P. S.; Burns, N. Z. J. Am. Chem. Soc. 2006, 128, 3908-3909
11. Woodard, B. T.; Posner, G. H. Adv. Cycloaddition 1999, 5, 47-83
12. Ono, N.; Kamimura, A.; Kaji, A. Tetrahedron Lett. 1986, 27, 1595-1598
13. Anderson, W. K.; Dewey, R. H. J. Am. Chem. Soc. 1973, 95, 7161-7162
14. Danishefsky, S.; Prisbylla, M. P.; Hiner, S. J. Am. Chem. Soc. 1978, 100, 2918-2920
15. Pindur, U.; Erfanian-Abdoust, H. Liebigs Ann. Chem. 1989, 12, 1275-1276
16. Pratt, A. J.; Rendle, P. M.; Steel, P. J. Aust. J. Chem. 2011, 64, 945-950
17. Hamann, P. R.; Toth, J. E.; Fuchs, P. L. J. Org. Chem. 1984, 49, 3865-3867
18. Natarajan, S.; Rajeswari, S.; Chandrasekaran, S.; Pai, B. R.; Shanmuganathan, S.; Rao, K. U. Ind. J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1982, 21, 95-97
19. Berger, D. M.; Birnberg, G.; DeMorin, F.; Dutia, M.; Powell, D.; Wang, Y. D. Synthesis 2003, 11, 1712-1716
20. Fukuyama, Y.; Yaso, H.; Mori, T.; Takahashi, H.; Minami, H.; Kodama, M. Heterocycles 2001, 54, 259-274
21. Marshall, J. A.; Gung, W. Y. Tetrahedron 1989, 45, 1043-1052
22. Dewey, R. S.; van Tamelen, E. E. J. Am. Chem. Soc. 1961, 83, 3729
23. Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652
24. Nelson, T. D.; Crouch, R. D. Org. React. 2004, 63, 265-555
25. Jones, S. B.; He, L.; Castle, S. L. Org. Lett. 2006, 8, 3757-3760
26. Kobayashi, S.; Okimoto, K.; Imakura, Y. Chem. Pharm. Bull. 1982, 30, 1567-1573
27. Clasby, M. C.; Craig, D.; Slawin, A. M. C.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 1509-1532
28. Okano, K.; Okuyama, K.-i.; Fukuyama, T.; Tokuyama, H. Synlett 2008, 13, 1977-1980
29. Ohira, S. Synth. Commun. 1989, 19, 561-564
30. Roth, G. J.; Liepold, B.; Mueller, S. G.; Bestmann, H. J. Synthesis 2004, 59-62