An enantioselective total synthesis of (+)-aigialospirol

Organic Letters

Volumn 9, Issue 23, 2007, Pages 4857-4859

  Figueroa, Ruth ^a   Hsung, Richard P ^a   Guevarra, Christie C ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AIGIALOSPIROL; BENZOFURAN DERIVATIVE; DRUG DERIVATIVE; HYPOTHEMYCIN; UNCLASSIFIED DRUG; ZEARALENONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BENZOFURANS; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; ZEARALENONE;

EID: 36349031275     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702195w     Document Type: Article

References (48)

1. Vongvilai, P.; Isaka, M.; Kittakoop, P. Prasert Srikitikulchai, P.; Kongsaeree, P.; Thebtaranonth, Y. J. Nat. Prod. 2004, 67, 457.
2. Faulkner, D. J. Nat. Prod. Rep. 2001, 18, 1.
3. (a) Nair, M. S. R.; Carey, S. T. Tetrahedron Lett. 1980, 21, 2011.
4. (b) Nair, M. S. R.; Carey, S. T.; James, J. C. Tetrahedron 1981, 37, 2445.
5. Revised structure of hypothemycin: Agatsuma, T.; Takahashi, A.; Kabuto, C.; Nozoe, S. Chem. Pharm. Bull. 1993, 41, 373.
6. For a leading review on syntheses of hypothemycin and related resorcylic macrolides, see: Winssinger, N.; Barluenga, S. Chem. Commun. 2007, 22.
7. For a total synthesis of hypothemycin, see: (a) Sellès, P.; Lett. R. Tetrahedron Lett. 2002, 43, 4621 and 4627.
8. For syntheses of other related resorcylic macrolides, see: (b) Yang, Z. Q.; Geng, X.; Solit, D.; Pratilas, C. A.; Rosen, N.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 7881.
9. (c) Barluenga, S.; Dakas, P. Y.; Ferandin, Y.; Meijer, L.; Winssinger, N. Angew. Chem., Int. Ed. 2006, 45, 3951.
10. (d) Lu, J.; Ma, J.; Xie, X.; Chen, B.; She, X.; Pan, X. Tetrahedron: Asymmetry 2006, 17, 1066.
11. (e) Grosche, P.; Akyel, K.; Marzinzik, A. Synthesis 2005, 2015.
12. (f) Garbaccio, R. M.; Stachel, S. J.; Baeschlin, D. K.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 10903.
13. (g) Lampilas, M.; Lett, R. Tetrahedron Lett. 1992, 33, 773 and 777.
14. Isaka, M.; Suyarnsestakorn, C.; Tanticharoen, M.; Kongsaeree, P.; Thebtaranonth, Y. J. Org. Chem. 2002, 67, 1561-1566.
15. (a) Tanaka, H.; Nishida, K.; Sugita, K.; Yoshioka, T. Jpn. J. Cancer Res. 1999, 90, 1139.
16. (b) Schirmer, A.; Kennedy, J.; Murli, S.; Reid, R.; Santi, D. V. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 4234.
17. (a) Ghosh, S. K.; Hsung, R. P.; Wang, J. Tetrahedron Lett. 2004, 45, 5505.
18. (b) Liu, J.; Hsung, R. P. Org. Lett. 2005, 7, 2273.
19. For reviews, see: (a) Aho, J. E.; Pihko, P. M.; Rissa, T. K. Chem. Rev. 2005, 105, 4406.
20. (b) Mead, K. T.; Brewer, B. N. Curr. Org. Chem. 2003, 7, 227.
21. (c) Brimble, M. A.; Fares, F. A. Tetrahedron 1999, 55, 7661.
22. (d) Fletcher, M. T.; Kitching, W. Chem. Rev. 1995, 95, 789.
23. (e) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617.
24. For related work, see: (a) Keller, V. A.; Martinellie, J. R.; Strieter, E. R.; Burke, S. D. Org. Lett. 2002, 4, 467.
25. (b) Kinderman, S. S.; Doodeman, R.; van Beijma, J. W.; Russcher, J. C.; Tjen, K. C. M. F.; Kooistra, T. M.; Mohaselzadeh, H.; van Maarseveen, J. H.; Hiemstra, H.; Schoemaker, H. E.; Rutjes, F. P. J. T. Adv. Synth. Catal. 2002, 344, 736.
26. (c) Leeuwenburgh, M. A.; Appeldoorn, C. C. M.; van Hooft, P. A. V.; Overkleeft, H. A.; van der Marel, G. A.; van Boom, J. H. Eur. J. Org. Chem. 2000, 837.
27. (d) Scholl, M.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 1425.
28. (e) Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247.
29. (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
30. (b) Hoveyda, A. H.; Schrock, R. R. Chem. - Eur. J. 2001, 7, 945.
31. (c) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592.
32. (d) Walters, M. A. In Progress in Heterocyclic Chemistry; Gribble, G. W., Joule, J., Eds. Pergamon: New York, 2003; Vol. 15, p 1.
33. (e) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127.
34. (f) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199.
35. (g) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239.
36. (h) Wallace, D. J. Angew. Chem., Int. Ed. 2005, 44, 1912.
37. See Supporting Information.
38. Hansen, T. V. Tetrahedron: Asymmetry 2002, 13, 547.
39. Khalaf, J. K.; Datta, A. J. Org. Chem. 2005, 70, 6937.
40. 2, see: (a) Sakakura, A.; Suzuki, K.; Nakano, K.; Ishihara, K. Org. Lett. 2006, 8, 2229.
41. (b) Sun, J.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127, 13512.
42. 2, see: (c) Thomazeau, C.; Olivier-Bourbigou, H.; Magna, L.; Luts, S.; Gilbert, B. J. Am. Chem. Soc. 2003, 125, 5264 and references cited therein.
43. (a) Ko, C.; Hsung, R. P. Org. Biomol. Chem. 2007, 7, 431.
44. (b) Ghosh, S. K.; Ko, C.; Liu, J.; Wang, J.; Hsung, R. P. Tetrahedron 2006, 62, 10485.
45. (a) Snieckus, V. Heterocycles 1980, 14, 1649.
46. (b) Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306.
47. (c) Snieckus, V. Chem. Rev. 1990, 90, 879.
48. (d) Anctil, E. J.-G.; Snieckus, V. J. Organomet. Chem. 2002, 653, 150.