An expeditious total synthesis of both diastereoisomeric lipid dihydroxytetrahydrofurans from Notheia anomala

Organic Letters

Volumn 14, Issue 9, 2012, Pages 2230-2233

  Roy, Sudeshna ^a   Spilling, Christopher D ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; FURAN DERIVATIVE; LIPID; PALLADIUM;

ARTICLE; BROWN ALGA; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKENES; CATALYSIS; CYCLIZATION; FURANS; LIPIDS; MOLECULAR STRUCTURE; PALLADIUM; PHAEOPHYTA; STEREOISOMERISM;

EID: 84860613439     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300597u     Document Type: Article

References (38)

1. Capon, R. J.; Barrow, R. A.; Rochfort, S.; Jobling, M.; Skene, C. Tetrahedron 1998, 54, 2227
2. Murray, L. M.; Barrow, R. A.; Capon, R. J. Aust. J. Chem. 1991, 44, 843
3. Barrow, R. A.; Capon, R. J. Aust. J. Chem. 1990, 43, 895
4. Warren, R. G.; Wells, R. J.; Blount, J. F. Aust. J. Chem. 1980, 33, 891
5. Gollner, A; Johann, M. Org. Lett. 2008, 10, 4701
6. Li, X.; Li, J.; Mootoo, D. R. Org. Lett. 2007, 9, 4303
7. Wang, J.; Pagenkopf, B. L. Org. Lett. 2007, 9, 3703
8. Jung, J. H.; Kim, Y. W.; Kim, M. A.; Choi, S. Y.; Chung, Y. K.; Kim, T.-R.; Shin, S.; Lee, E. Org. Lett. 2007, 9, 3225
9. Evans, D. A.; Kvaerno, L.; Mudler, J. A.; Raymer, B.; Dunn, T. B.; Beauchamin, A.; Olhava, E. J.; Juhl, M.; Kagechika, K. Angew. Chem., Int. Ed. 2007, 46, 4693
10. Evans, P. A.; Murthy, V. S.; Roseman, J. D.; Rheingold, A. L. Angew. Chem., Int. Ed. 1999, 38, 3175
11. Williams, D. R.; Harigaya, Y.; Moore, J. L. J. Am. Chem. Soc. 1984, 106, 2641
12. Capon, R. J.; Barrow, R. A. J. Org. Chem. 1998, 63, 75
13. Capon, R. J.; Barrow, R. A.; Skene, C.; Rochfort, S. Tetrahedron Lett. 1997, 38, 7609
14. Nesbitt, C. L.; McErlean, C. S. P. Tetrahedron Lett. 2009, 50, 6318
15. de la Pradilla, R. F.; Castellanos, A.; Osante, I.; Colomer, I.; Sanchez, M. I. J. Org. Chem. 2009, 74, 170
16. de la Pradilla, R. F.; Castellanos, A. Tetrahedron Lett. 2007, 48, 37
17. Mori, Y.; Sawada, T.; Furukawa, H. Tetrahedron Lett. 1999, 40, 731
18. Chikashita, H.; Nakamura, Y.; Uemura, H.; Itoh, K. Chem. Lett. 1993, 477
19. Gurjar, M. K.; Mainkar, P. S. Heterocycles 1990, 31, 407
20. Hatakeyama, S.; Sakurai, K.; Saijo, K.; Takano, S. Tetrahedron Lett. 1985, 26, 1333
21. Gadikota, R. R.; Callam, C. S.; Lowary, T. L. J. Org. Chem. 2001, 66, 9046
22. Yoda, H.; Maruyama, K.; Takabe, K. Tetrahedron: Asymmetry 2001, 12, 1403
23. Nesbitt, C. L.; McErlean, C. S. P. Org. Biomol. Chem. 2011, 9, 2198
24. Gracia, C.; Martin, T.; Martin, V. S. J. Org. Chem. 2001, 66, 1420
25. Gracia, C.; Soler, M. A.; Martin, V. S. Tetrahedron Lett. 2000, 41, 4127
26. Kang, B.; Mowat, J.; Pinter, T.; Britton, R. Org. Lett. 2009, 11, 1717
27. Mowat, J.; Kang, B.; Fonovic, B.; Dudding, T.; Britton, R. Org. Lett. 2009, 11, 2057
28. He, A.; Sutivisedsak, N.; Spilling, C. D. Org. Lett. 2009, 11, 3124
29. Roy, S.; Spilling, C. D. Org. Lett. 2010, 12, 5326
30. Jiao, P.; Kawasaki, M.; Yamamoto, H. Angew. Chem., Int. Ed. 2009, 48, 3333
31. He, A.; Yan, B.; Thanavaro, A.; Spilling, C. D. J. Org. Chem. 2004, 69, 8643
32. Rivard, M.; Blechert, S. Eur. J. Org. Chem. 2003, 2225
33. Voigtritter, K; Ghorai, S.; Lipshutz, B. H. J. Org. Chem. 2011, 76, 4697
34. Kim, S.-G.; Park, T.-H.; Kim, B. J. Tetrahedron Lett. 2006, 47, 6369
35. Roulland, E. Angew. Chem., Int. Ed. 2008, 47, 3762
36. Chunguang, H.; Uemura, D. Tetrahedron Lett. 2008, 49, 6988
37. Ma, C.; Schiltz, S.; Le Goff, X. F.; Prunet, J. Chem.-Eur. J. 2008, 14, 7314
38. Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887