Enantioselective Synthesis of (+)-O-Trimethylsappanone B and (+)-O-Trimethylbrazilin

Journal of Organic Chemistry

Volumn 58, Issue 7, 1993, Pages 1751-1753

  Davis, Franklin A ^a   Chen, Bang Chi ^a  

^a DREXEL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HOMOISOFLAVONE DERIVATIVE; O TRIMETHYLBRAZILIN; O TRIMETHYLSAPPANONE B; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0027309035     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00059a026     Document Type: Article

References (33)

1. For reviews on the chemistry of brazilin see: (a) Robinson, R. Bull. Soc. Chim. Fr. 1958, 125.
2. Robinson, R. In Chemistry of Carbon Compounds; Rodd, F. H., Ed.; Elsevier: Amsterdam, 1959; Vol. IVB, p 1005.
3. Cheveul, M. Ann. Chim. 1808, 66, 225.
4. Namikoshi, M.; Nakata, H.; Yamada, H.; Nagai, M.; Saitoh, T. Chem. Pharm. Bull. 1987, 35, 2761.
5. Heller, W.; Tamm, C. Fortschr. Chem. Org. Naturst. 1981, 40, 105.
6. Livingstone, R. Nat. Prod. Rep. 1987, 4, 25.
7. Gupta, M. P.; Gupta, N. P. Curr. Sci. 1968, 37, 250;
8. Chem. Abstr. 1968, 69, 39531y.
9. Pratt, R.; Yuzuriha, Y. J. Am. Pharm. Assoc. 1959, 48, 69.
10. Hikino, H.; Taguchi, T.; Fujimura, H.; Hiramatsu, Y. Planta Med. 1977, 31, 214.
11. Moon, C. K.; Chung, J. H.; Choi, S. S.; Lee, S. H.; Hwang, G. S.; Park, K. S.; Mock, M. S.; Kim, S. G.; Kim, J. Y. Arch. Pharmacal. Res. 1988, 11, 145.
12. Moon, C. K.; Chung, J. H.; Lee, Y. M.; Lee, S. H.; Hwang, G. S.; Park, K. S.; Mock, M. S.; Kim, S. G.; Ahn, Y. S.; Ann, J. H. Arch. Pharmacal. Res. 1988, 11, 149.
13. Namikoshi, M.; Nakata, H.; Nuno, M.; Ozawa, T.; Saitoh, T. Chem. Pharm. Bull. 1987, 35, 3568.
14. Saitoh, T.; Sakashita, S.; Nakata, H.; Shimokawa, T.; Kinjo, J.-E.; Yamahara, J.; Yamasaki, M.; Nohara, T. Chem. Pharm. Bull. 1986, 34, 2506.
15. Chiang Su New Medical College, Ed. Dictionary of Chinese Crude Drugs; Shanghai Scientific Technologic Publisher: Shanghai, 1977; p 1083.
16. Kirkiacharian, B. S. C. R. Acad. Ser. Ser. C. 1972, 274, 2096.
17. Kirkiacharian, B. S.; Billet, D.; Durgeat, M.; Heitz, S.; Adjangba, M. K. Bull. Soc. Chim. Fr. 1975, 1770.
18. Dann, O.; Hofmann, H. Justus Liebigs Ann. Chem. 1963, 667, 116.
19. Davis, F. A.; Chen, B. C. Tetrahedron Lett. 1990, 31, 6823.
20. Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703.
21. Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919.
22. Davis, F. A.; Chen, B.-C. Asymmetric Oxygenation of Enolates. In Stereoselective Synthesis of Organic Compounds; Houben-Weyl: Methoden der Organischen Chemie; GeorgThieme Verlag: Stuttgart; in press.
23. Davis, F. A.; Kumar, A.; Chen, B.-C. J. Org. Chem. 1991, 56, 1143.
24. Davis, F. A.; Kumar, A.; Chen, B.-C. Tetrahedron Lett. 1991, 32, 867.
25. Davis, F. A.; Weismiller, M. C. J. Org. Chem. 1990, 55, 3715.
26. Davis, F. A.; Kumar, A. Tetrahedron Lett. 1991, 32, 7671.
27. Davis, F. A.; Weismiller, M. C.; Murphy, C. K.; Thimma Reddy, R.; Chen, B.-C. J. Org. Chem. 1992, 57, 7274–7285.
28. Namikoshi, M.; Saitoh, T. Chem. Pharm. Bull. 1987, 35, 3597.
29. Davis, F. A.; Thimma Reddy, R.; Han, W.; Carroll, P. J. J. Am. Chem. Soc. 1992, 114, 1428.
30. Shah, V. R.; Joshi, C. G.; Kulkami, A. B. Chem. Ind. 1965, 1062.
31. Schiavello, A.; Sebastiani, C. Gazz. Chim. Ital. 1949, 79, 909.
32. Jain, A. C.; Sharma, A.; Srivastava, R. Indian J. Chem. Sect. B 1983, 22B, 1119.
33. Pinkey; Jain, P. K.; Grover, S. K. Indian J. Chem. Sect. B 1986, 25B, 365.