Convergent Synthesis of (±)-Dihydroisocodeine in 11 Steps by the Tandem Radical Cyclization Strategy. A Formal Total Synthesis of (±)-Morphinet

Journal of the American Chemical Society

Volumn 114, Issue 24, 1992, Pages 9688-9689

  Parker, Kathlyn A ^a   Fokas, Demosthenes ^a  

^a BROWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROISOCODEINE; MORPHINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0027075049     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00050a075     Document Type: Letter

References (33)

1. Lednicer, D. Central Analgetics; John Wiley & Sons, Inc.: New York, 1982; pp 137-213.
2. Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959.
3. Magnus, P.; Coldham, I. J. Am. Chem. Soc. 1991, 113, 672.
4. Rieke, R. D.; Schulte, L. D.; Dawson, B. T.; Yang, S. S. J. Am. Chem. Soc. 1990, 112, 8388.
5. Lee, E.; Shin, I.-J.; Kim, T.-S. J. Am. Chem. Soc. 1990, 112, 260.
6. Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130.
7. Parker, K. A.; Spero, D. M.; Inman, K. C. Tetrahedron Lett. 1986, 27, 2833.
8. Parker, K. A.; Spero, D. M.; Van Epp, J. J. Org. Chem. 1988, 53, 4628.
9. Makleit, S.; Bognár, R. Acta Chim. Acad. Sci. Hung. 1969, 59, 387.
10. Gates, M.; Woodward, R. B.; Newhall, W. F.; Künzli, R. J. Am. Chem. Soc. 1950, 72, 1141.
11. Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109.
12. Toth, J. E.; Hamann, P. R.; Fuchs, P. L. J. Org. Chem. 1988, 53, 4694.
13. Broka, C. A.; Gerlits, J. F. J. Org. Chem. 1988, 53, 2144.
14. Sdassi, H.; Revial, G.; Pfau, M.; d'Angelo, J. Tetrahedron Lett. 1990, 31, 875.
15. Monkovic, I.; Wong, H. Can. J. Chem. 1976, 54, 883.
16. Chandler, M.; Parsons, P. J. J. Chem. Soc., Chem. Commun. 1984, 322.
17. Gagné, M. R.; Stem, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275.
18. Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 3839.
19. Gemal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 5454.
20. Morgans, D. J., Jr.; Sharpless, K. B.; Traynor, S. G. J. Am. Chem. Soc. 1981, 103, 462.
21. Mitsunobu, O. Synthesis 1981, 1.
22. Chatgilialoglu, C.; Griller, D.; Lesage, M. J. Org. Chem. 1989, 54, 2492.
23. Heathcock, C. H.; Smith, K. M.; Blumenkopf, T. A. J. Am. Chem. Soc. 1986, 108, 5022.
24. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493.
25. Closson, W. D.; Ji, S.; Schulenberg, S. J. Am. Chem. Soc. 1970, 92, 650.
26. Newcomb, M.; Deeb, T. M.; Marquardt, D. J. Tetrahedron 1990, 46, 2317.
27. Weller, D. D.; Rapoport, H. J. Med. Chem. 1976, 19, 1171.
28. Iijima, I.; Rice, K. C.; Silverton, J. V. Heterocycles 1977, 6, 1157.
29. Rice, K. C. J. Med. Chem. 1977, 20, 164.
30. Lawson, J. A.; DeGraw, J. I. J. Med. Chem. 1977, 20, 165.
31. Hazlet, S. E.; Brotherton, R. J. J. Org. Chem. 1962, 27, 3253.
32. Green, M. J. Chem. Soc. 1963, 1324.
33. Corey, E. J.; Shulman, J. I. J. Org. Chem. 1970, 35, 777.