Synthesis of the azaphilones using copper-mediated enantioselective oxidative dearomatization

Journal of the American Chemical Society

Volumn 127, Issue 26, 2005, Pages 9342-9343

  Zhu, Jianglong ^a   Grigoriadis, Nicholas P ^a   Lee, Jonathan P ^a   Porco Jr , John A ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; HETEROCYCLIC COMPOUND;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; ENANTIOSELECTIVITY; ISOMERIZATION; OXIDATION; OXIDATIVE DEAROMATIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

BENZOPYRANS; CATALYSIS; COPPER; LIGANDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PIGMENTS, BIOLOGICAL; SOLVENTS; STEREOISOMERISM; TEMPERATURE;

EID: 21644436580     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052049g     Document Type: Article

References (32)

1. Kono, K.; Tanaka, M.; Ono, Y.; Hosoya, T.; Ogita, T.; Kohama, T. J. Antibiot. 2001, 54, 415.
2. Zhu, J.; Germain, A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239.
3. (a) Chong, R.; King, R. R.; Whalley, W. B. J. Chem. Soc. C 1971, 3566.
4. (b) Chong, R.; King, R. R.; Whalley, W. B. J. Chem. Soc. C1971, 3571.
5. (c) Suzuki, T.; Okada, C.; Arai, K.; Awall, A.; Shimizu, T.; Tanemura, K.; Horaguchi, T. J. Helerocycl. Chem. 2001, 38, 1409.
6. Stark, L. M.; Pekari, K.; Sorensen, E. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12064.
7. (a) Karlin, K. D.; Tyeklar, Z. Bioinorganic Chemistry of Copper; Chapman & Hall: New York, 1993.
8. (b) Stephenson, G. R. Adv. Asymmetric Synth. 1996, 367.
9. Colombo, L.; Scolastico, C.; Lukacs, G.; Dessinges, A.; Aragozzini, F.; Merendi, C. J. Chem. Soc., Chem. Commun. 1983, 1436.
10. (a) Robert, A.; Meunier, B. Asymmetric Biomimetic Oxidations. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B., Ed.; Imperial College Press. London, 2000; p 543.
11. (b) Gamez, P.; Aubel, P. G.; Driessen, W. L.; Reedijk, J. Chem. Soc. Rev. 2001, 10, 376.
12. Hashmi, A. S. K. Gold Bull. 2004, 37, 51.
13. See Supporting Information for further details.
14. (a) Mirica, L. M.; Vance, M.; Rudd, D. J.; Hedman, B.; Hodgson, K. O.; Solomon, E. I.; Stack, T. D. P. J. Am. Chem. Soc. 2002, 124, 9332.
15. (b) Stack, T. D. P. J. Chem. Soc., Dalton Trans. 2003, 1881.
16. Recent reviews: (c) Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Chem. Rev. 2004, 104, 1013.
17. Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047.
18. (e) Hatcher, L. Q.; Karlin, K. D. J. Biol. Inorg. Chem. 2004, 9, 669.
19. Hanessian, S.; Meffre, P.; Girard, M.; Beaudoin, S.; SancBau, J.-Y.; Bennani, Y. J. Org. Chem. 1993, 58, 1991.
20. (a) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-i. J. Org. Chem. 1999, 64, 2264.
21. (b) Funahashi, Y.; Nakaya, K.; Hirota, S.; Yamauchi, O. Chem. Lett. 2000, 1172.
22. (c) Zhang, Y.; Yeung, S.-M.; Wu, H.; Heller, D. P.; Wu, C.; Wulff, W. D. Org. Lett. 2003, 5, 1813.
23. For palladium-catalyzed oxidative kinetic resolution using (-)-sparteine as ligand, see: (d) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725.
24. (e) Mueller, J. A.; Jensen, D. R.; Sigman, M. S. J. Am. Chem. Soc. 2002, 124, 8202.
25. Diastereoselective oxidative dearomatization: (a) Pettus, L. H.; Van De Water, R. W.; Pettus, T. R. R. Org. Lett. 2001, 3, 905.
26. (b) Mejorado, L. H.; Hoarau, C.; Pettus, T. R. R. Org. Lett. 2004, 6, 1535.
27. Malkov, A. V.; Baxendale, I. R.; Bella, M.; Langer, V.; Fawcett, J.; Russell, D. R.; Mansfield, D. J.; Valko, M.; Kocovsky, P. Organometallics 2001, 20, 673.
28. (a) Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 1381.
29. (b) Marko, I. E.; Gautier, A.; Dumeunier, R.; Doda, K.; Philippart, F.; Brown, S. M.; Urch, C. J. Angew. Chem., Int. Ed. 2004, 43, 1588.
30. Base-mediated 6-endo-dig cycloisomerization of ynones: Alvaro, M.; Garcia, H.; Iborra, S.; Miranda, M. A.; Primo, J. Tetrahedron 1987, 43, 143.
31. (a) Vleggaar, R.; Steyn, P. S.; Nagel, D. W. J. Chem. Soc., Perkin Trans. 1 1974, 45.
32. (b) Steyn, P. S.; Vleggaar, R. J. Chem. Soc., Perkin Trans. 1 1976, 204.