An efficient synthesis of the fully elaborated isoindolinone unit of muironolide A

Organic Letters

Volumn 15, Issue 13, 2013, Pages 3314-3317

  Xiao, Qing ^a   Young, Kyle ^a   Zakarian, Armen ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXENE DERIVATIVE; ESTER; ISOINDOL 1 ONE; ISOINDOL-1-ONE; ISOINDOLE DERIVATIVE; MUIRONOLIDE A;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLIZATION; CYCLOHEXENES; ESTERS; ISOINDOLES; STEREOISOMERISM;

EID: 84880019814     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401354a     Document Type: Article

References (37)

1. Dalisay, D. S.; Morinaka, B. I.; Skepper, C. K.; Molinski, T. F. J. Am. Chem. Soc. 2009, 131, 7552-7553
2. Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117, 8126-8131
3. Searle, P. A.; Molinski, T. F.; Brzezinski, L. J.; Leahy, J. W. J. Am. Chem. Soc. 1996, 118, 9422-9423
4. Molinski, T. F. Nat. Prod. Rep. 2010, 27, 321-329
5. Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41-61
6. Brieger, G.; Bennet, J. N. Chem. Rev. 1980, 80, 63-97
7. Ciganek, E. Org. React. 1984, 32, 1-374
8. Roush, W. R. Intramolecular Diels-Alder Reactions. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, pp 513-550.
9. Winkler, J. D. Chem. Rev. 1996, 96, 167-176
10. Bear, B. R.; Sparks, S. M.; Shea, K. J. Angew. Chem., Int. Ed. 2001, 40, 820-849
11. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698
12. Takao, K.-i.; Munakata, R.; Tadano, K.-i. Chem. Rev. 2005, 105, 4779-4807
13. Tadano, K.-i. Eur. J. Org. Chem. 2009, 4381-4394
14. Juhl, M.; Tanner, D. Chem. Soc. Rev. 2009, 38, 2983-2992
15. Flores, B.; Molinski, T. F. Org. Lett. 2011, 13, 3932-3935
16. For an example of a strategic application of an IMDA reaction involving an enol derived from a β-keto carbonyl precursor as a diene counterpart, see: Scheerer, J. R.; Lawrence, J. F.; Wang, G. C.; Evans, D. A. J. Am. Chem. Soc. 2007, 129, 8968-8969
17. Boeckman, R. K., Jr.; Thomas, A. J. J. Org. Chem. 1982, 47, 2823-2824
18. Yamashita, M. Y.; Yasumoto, T.; Rawal, V. H. Heterocycles 1998, 48, 79-93
19. Babler, J. M.; Buttner, W. J. Tetrahedron Lett. 1976, 17, 239-241
20. Van, T. N.; De Kimpe, N. Tetrahedron 2000, 56, 7969-7973
21. Duboudin, J. G.; Jousseaume, B.; Saux, A. J. Organomet. Chem. 1979, 168, 1-11
22. Liu, F.; Negishi, E. J. Org. Chem. 1997, 62, 8591-8594
23. Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772-10773
24. Clausen, D. J.; Wan, S.; Floreancig, P. E. Angew. Chem., Int. Ed. 2011, 50, 5178-5181
25. Reber, K. P.; Tilley, S. D.; Sorensen, E. J. Chem. Soc. Rev. 2009, 38, 3022-3034
26. Clemens, R. J.; Witzeman, J. S. J. Am. Chem. Soc. 1989, 111, 2186-2193
27. Yang, Z.; Shannon, D.; Truong, V.-L.; Deslongchamps, P. Org. Lett. 2002, 4, 4693-4696
28. Petrovic, D.; Brückner, R. Org. Lett. 2011, 13, 6524-6527
29. Xue, H.; Yang, J.; Gopal, P. Org. Lett. 2011, 13, 5696-5699
30. Stivala, C. E.; Zakarian, A. J. Am. Chem. Soc. 2008, 130, 3774-3776
31. Stivala, C. E.; Zakarian, A. Org. Lett. 2009, 11, 839-842
32. Araoz, R.; Servent, D.; Molgo, J.; Iorga, B. I.; Fruchart-Gaillard, C.; Benoit, E.; Gu, Z.; Stivala, C.; Zakarian, A. J. Am. Chem. Soc. 2011, 133, 10499-10511
33. Stivala, C. E.; Zakarian, A. Tetrahedron Lett. 2007, 48, 6845-6848
34. Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783-3784
35. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179
36. Dewi, P.; Randl, S.; Blechert, S. Tetrahedron Lett. 2005, 46, 577-580
37. For an example of an IMDA reaction with silyl enol ethers derived from β-keto carbonyl compounds, see: Grimaud, L.; Ferezou, J.-P.; Prunet, J.; Lallemand, J.-Y. Tetrahedron 1997, 53, 9253-9268 of General Medical Sciences