A tandem cascade cyclization-electrophilic aromatic substitution: Application in the total synthesis of (+)-angelichalcone

Journal of the American Chemical Society

Volumn 131, Issue 41, 2009, Pages 14630-14631

  Topczewski, Joseph J ^a   Callahan, Michael P ^a   Neighbors, Jeffrey D ^a   Wiemer, David F ^a  

^a E11 SSH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; CYCLIZATIONS; ELECTROPHILIC AROMATIC SUBSTITUTIONS; LEWIS ACID; REGIO-SELECTIVE; TANDEM CASCADE; TANDEM PROCESS; TOTAL SYNTHESIS;

CYCLIZATION; PHENOLS;

SYNTHESIS (CHEMICAL);

CHALCONE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

CHALCONE; CYCLIZATION; STEREOISOMERISM; SUBSTRATE SPECIFICITY; XANTHENES;

EID: 70350070379     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja906468v     Document Type: Article

References (22)

1. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134-7186.
2. Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551-564.
3. Neighbors, J. D.; Beutler, J. A.; Wiemer, D. F. J. Org. Chem. 2005, 70, 925-931.
4. Mente, N. R.; Neighbors, J. D.; Wiemer, D. F. J. Org. Chem. 2008, 73, 7963-7970.
5. Neighbors, J. D.; Topczewski, J. J.; Wiemer, D. F. Tetrahedron Lett. 2009, 50, 3881-3884.
6. Kartika, R.; Frein, J. D.; Taylor, R. E. J. Org. Chem. 2008, 73, 5592-5594.
7. Bellucci, G.; Bianchini, R.; Chiappe, C.; Marioni, F.; Spagna, R. J. Am. Chem. Soc. 1988, 110, 546-552.
8. Paul, S.; Nanda, P.; Gupta, R.; Loupy, A. Synthesis 2003, 2877-2881.
9. Selvam, J. J. P.; Suresh, V.; Rajesh, K.; Reddy, S. R.; Venkateswarlu, Y. Tetrahedron Lett. 2006, 47, 2507-2509.
10. Reggelin, M.; Doerr, S. Synlett 2004, 1117.
11. Buschek, J. M.; Holmes, J. L.; Terlouw, J. K. J. Am. Chem. Soc. 1987, 109, 7321-7325.
12. Trost, B. M. Science 1991, 254, 1471-1477.
13. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281.
14. Ohnogi, H.; Sugiyama, K.; Muraki, N.; Sagawa, H.; Kato, I. U.S. Patent US20060039998, Feb 23, 2006.
15. Akihisa, T.; Tokuda, H.; Ukiya, M.; Iizuka, M.; Schneider, S.; Ogasawara, K.; Mukainaka, T.; Iwatsuki, K.; Suzuki, T.; Nishino, H. Cancer Lett. 2003, 201, 133-137.
16. Aoki, N.; Muko, M.; Ohta, E.; Ohta, S. J. Nat. Prod. 2008, 71, 1308-1310.
17. Townsend, C. A.; Davis, S. G.; Christensen, S. B.; Link, J. C.; Lewis, C. P. J. Am. Chem. Soc. 1981, 103, 6885-6888.
18. Gansauer, A.; Justicia, J.; Rosales, A.; Rinker, B. Synlett 2005, 1954-1956.
19. Neighbors, J. D.; Mente, N. R.; Boss, K. D.; Zehnder, D. W., II; Wiemer, D. F. Tetrahedron Lett. 2008, 49, 516-519.
20. Lee-Ruff, E.; Ablenas, F. J. Can. J. Chem. 1989, 67, 699-702.
21. Topczewski, J. J.; Neighbors, J. D.; Wiemer, D. F. J. Org. Chem. 2009, 74, 6965-6972.
22. The relative stereochemistry of the cyclization was assigned in a fashion parallel to that for compound 9. Neither the absolute stereochemistry nor the rotation was reported for angelichalcone in the original report. The synthetic material described here has (2R,4aR,9aR) stereochemistry.