Cycloadditions of o-quinone dimethides with p-quinol derivatives: Regiocontrolled formation of anthracyclic ring systems

Tetrahedron Letters

Volumn 45, Issue 8, 2004, Pages 1793-1796

  Wang, Junhua ^a   Pettus, Liping H ^a   Pettus, Thomas R R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACYCLINE DERIVATIVE; KETONE DERIVATIVE; NATURAL PRODUCT; QUINONE DERIVATIVE; RISHIRILIDE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CYCLOADDITION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0842348267     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.114     Document Type: Article

References (23)

1. Brizzi R.S., Roos G.H.P. S. Afr. J. Chem. 38:1985;150-152.
2. Hauser F.M., Xu Y.-J. Org. Lett. 1:1999;335-336.
3. Freskos J.N., Morrow G.W., Swenton J.S. J. Org. Chem. 50:1985;805-810.
4. Deshpande P.P., Price K.N., Baker D.C. J. Org. Chem. 61:1996;455.
5. Bates M.A., Sammes P.G., Thomson G.A. J. Chem. Soc., Perkin Trans. 1. 1988;3037.
6. Hamura T., Hosoya T., Yamaguchi H., Kuriyama Y., Tanabe M., Miyamoto M., Yasui Y., Matsumoto T., Suzuki K. Helv. Chim. Acta. 85:2002;3589.
7. Allen J.G., Danishefsky S.J. J. Am. Chem. Soc. 123:2001;351-352.
8. Yamamoto K., Hentemann M.F., Allen J.G., Danishefsky S.J. Chem. Eur. J. 9:2003;3242-3252.
9. Sammes P.G. Tetrahedron. 32:1976;405.
10. Van De Water R.W., Hoarau C., Pettus T.R.R. Tetrahedron Lett. 44:2003;5109-5113.
11. Mejorado, L.; Pettus, T. R. R. Unpublished results.
12. Borowitz I.J., Kibby K.C. Jr., Virkhalls R. J. Org. Chem. 31:1966;4031.
13. Zimmerman H.E., Cassel J.M. J. Org. Chem. 54:1989;3800.
14. Durst T., Kozma E.C., Charlton J.L. J. Org. Chem. 50:1985;4829-4833.
15. Comins D.L., Brown J.D. J. Org. Chem. 54:1989;3730-3732.
16. Compound 26 can also be constructed according to: Leeds A.R., Boettger S.D., Ganem B. J. Org. Chem. 45:1980;1098.
17. Pettus T.R.R., Van De Water R.W., Magdziak D., Chau J. J. Am. Chem. Soc. 122:2000;6502-6503.
18. Jones R.M., Van De Water R.W., Lindsey C., Hoarau C., Ung T., Pettus T.R.R. J. Org. Chem. 66:2001;3435-3441.
19. Tuttle K., Rodriguez A.A., Pettus T.R.R. Synlett. 2003;2234-2237.
20. Hoarau C., Pettus T.R.R. Synlett. 2003;127-137.
21. Lindsey C., Gomez-Diaz C., Villalba J.M., Pettus T.R.R. Tetrahedron. 58:2002;4559-4565.
22. Chen W.-M. Indian J. Chem., Sect. B. 35B:1996;1085-1087.
23. Bui E., Bayle J.P., Perez F., Liebert L., Courtieu J. Liq. Cryst. 8:1990;513-526.