Acid-induced rearrangement reactions of reduced benzoquinone cyclopentadiene cycloadducts

Journal of Organic Chemistry

Volumn 67, Issue 24, 2002, Pages 8692-8695

  Eipert, Martin ^a   Maichle Mössmer, Cäcilia ^a   Maier, Martin E ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ORGANIC ACIDS; REDUCTION; X RAY ANALYSIS;

REARRANGEMENT REACTIONS;

AROMATIC COMPOUNDS;

BENZOQUINONE; CYCLOPENTADIENE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DIELS ALDER REACTION; DRUG ISOLATION; REACTION ANALYSIS; SOLUBILIZATION; THIN LAYER CHROMATOGRAPHY; X RAY ANALYSIS;

EID: 2242417388     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026238i     Document Type: Article

References (29)

1. Money, T. Nat. Prod. Rep. 1985, 253-289.
2. Jacobsen, N.; Torssell, K. Liebigs Ann. Chem. 1972, 763, 135-147.
3. Jockers, R.; Schmid, R. D.; Rieger, H.; Krohn, K. Liebigs Ann. Chem. 1991, 315-321.
4. Al-Hamdany, R.; Bruce, J. M.; Heatley, F.; Khalafy, J. J. Chem. Soc., Perkin Trans. 2 1985, 1395-1400.
5. Wegner, G.; Keyes, T. F., III; Nakabayashi, N.; Cassidy, H. G. J. Org. Chem. 1969, 34, 2822-2826.
6. Borchardt, R. T.; Cohen, L. A. J. Am. Chem. Soc. 1972, 94, 9175-9182.
7. Alder, K.; Flock, F. H.; Beumling, H. Chem. Ber. 1960, 93, 1896-1899.
8. Ichihara, A.; Kobayashi, M.; Oda, K.; Sakamura, S. Bull. Chem. Soc. Jpn. 1978, 51, 826-829.
9. Shimizu, M.; Kamikubo, T.; Ogasawara, K. Heterocycles 1997, 41, 21-26.
10. Wu, H.,J.; Chao, C.-S.; Lin, C.-C. J. Org. Chem. 1998, 63, 7687-7693.
11. Reetz, M. T. Adv. Organomet. Chem. 1977, 16, 33-65.
12. Black, T. H.; DuBay, W. J., III; Tully, P. S. J. Org. Chem. 1988, 53, 5922-5927.
13. Mulzer, J.; Hoyer, K.; Müller-Fahrnow, A. Angew. Chem. 1997, 109, 1546-1548;
14. Angew. Chem., Int. Ed. Engl. 1997, 36, 1476-1478.
15. Osterhage, C.; König, G. M.; Höller, U.; Wright, A. D. J. Nat. Prod. 2002, 65, 306-313.
16. Rösslein, L.; Tamm, C.; Zürcher, W.; Riesen, A.; Zehnder, M. Helv. Chim. Acta 1988, 71, 588-595.
17. Zhang, S.-X.; Chen, K.; Liu, X.-J.; Zhang, D.-C.; Tao-Wiedmann, T.-W.; Leu, S.-L.; McPhail, A. T.; Lee, K.-H. J. Nat. Prod. 1995, 58, 540-547.
18. Matsuo, A.; Nozaki, H.; Yano, K.; Uto, S.; Nakayama, M.; Huneck, S. Phytochemistry 1990, 29, 1921-1925.
19. Langer, P.; Holtz, E.; Saleh, N. N. R. Chem. Eur. J. 2002, 8, 917-928.
20. (a) Büchi, G.; Chu, P.-S. J. Am. Chem. Soc. 1979, 101, 6767-6768.
21. (b) Engler, T. A.; Wei, D.; Letavic, M. A. Tetrahedron Lett. 1993, 34, 1429-1432.
22. Hoye, T. R. Tetrahedron Lett. 1981, 22, 2523-2526.
23. Coates, R. M.; Shah, S. K.; Mason, R. W. J. Am. Chem. Soc. 1979, 101, 6765-6767.
24. Welch, S. C.; Chayabunjonglerd, S. J. Am. Chem. Soc. 1979, 101, 6768-6769.
25. Trost, B. M.; McDougal, P. G. J. Am. Chem. Soc. 1982, 104, 6110-6111.
26. O'Neil, S. V.; Quickley, C. A.; Snider, B. B. J. Org. Chem. 1997, 62, 1970-1975.
27. Haney, B.; Curran, D. P. J. Org. Chem. 2000, 65, 2007-2013.
28. Kodama, M.; Kurihara, T.; Sasaki, J.; Itô, S. Can. J. Chem. 1979, 57, 3343-3345.
29. Monti, S. A.; Dean, T. R. J. Org. Chem. 1982, 47, 2679-2681.