Rearrangement of 5-trimethylsilylthebaine on treatment with L-selectride: An efficient synthesis of (+)-bractazonine

Journal of Organic Chemistry

Volumn 68, Issue 5, 2003, Pages 1929-1932

  Chen, Weibin ^a   Wu, Huifang ^a   Bernard, Denzil ^a   Metcalf, Matthew D ^a   Deschamps, Jeffrey R ^b   Flippen Anderson, Judith L ^b   MacKerell Jr , Alexander D ^a   Coop, Andrew ^a  

^a UNIVERSITY OF MARYLAND SCHOOL OF PHARMACY   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INORGANIC ACIDS; POSITIVE IONS; REDUCTION; SYNTHESIS (CHEMICAL);

LEWIS ACIDS;

BENZENE;

10 TRIMETHYLSILYLBRACTAZONINE; 5 TRIMETHYLSILYLTHEBAINE; ALKYL GROUP; BRACTAZONINE; LEWIS ACID; LITHIUM ION; PHENYL GROUP; SELECTRIDE; THEBAINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

ALKALOIDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STEREOISOMERISM; THEBAINE;

EID: 0037424329     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020704m     Document Type: Article

References (16)

1. Casy, A. F.; Parfitt, R. T. Opioid Analgesics; Plenum Press: New York and London, 1986.
2. United States Food and Drug Administration, FDA Talk Paper T02-38, October 8, 2002.
3. Qin, B. Y. Drug Dev. Res. 1996, 39, 131.
4. Coop, A.; Janetka, J. W.; Lewis, J. W.; Rice, K. C. J. Org. Chem. 1998, 63, 4392.
5. Coop, A.; Lewis, J. W.; Rice, K. C. J. Org. Chem. 1996, 61, 6774.
6. Boden, R. M.; Gates, M.; Ho, S. P.; Sundararaman, P. J. Org. Chem. 1982, 47, 1347.
7. Maat, L.; Woudenberg, R. H.; Meuzelaar, G. J.; Linders, J. T. Bioorg. Med. Chem. 1999, 7, 529.
8. Woudenberg, R. H.; Oosterhoff, B. E.; Maat, L. Recl. Trav. Chim, Pays Bas. 1992, 111, 119.
9. Theuns, H. G.; Lenting, H. B. M.; Salemink, C. A.; Tanaka, H.; Shibata, M.; Lousberg, R. J. J. C. Phytochemistry 1984, 23, 1157.
10. Bentley, K. W. J. Am. Chem. Soc. 1967, 89, 2464.
11. Bentley, K. W.; Lewis, J. W.; Talyor, J. B. J. Chem. Soc. 1969, 1945.
12. Channon, R. T.; Kirby, G. W.; Massey, S. R. J. Chem. Soc. 1969, 1215.
13. Theuns, H. G.; La Vos, G. F.; ten Noever de Brauw, M. C.; Salemink, C. A. Tetrahedron Lett. 1984, 37, 4161.
14. Kupchan, S. M.; Kim, C.-K. J. Am. Chem. Soc. 1975, 97, 5623.
15. Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Termura, D. H. J. Am. Chem. Soc. 1987, 109, 9, 7838.
16. Kofron, W. G.; Baclawski, L. M. J. Org. Chem. 1976, 41, 1879.