Chemoenzymatic total synthesis of (+)-codeine by sequential intramolecular Heck cyclizations via C-B-D ring construction

Synlett

Volumn , Issue 18, 2007, Pages 2859-2862

  Omori, Alvaro T ^a   Finn, Kevin J ^a   Leisch, Hannes ^a   Carroll, Robert J ^a   Hudlicky, Tomas ^a  

^a BROCK UNIVERSITY   (Canada)

Author keywords

Codeine; Enzymatic dihydroxylation; Hydroamination; Sequential intramolecular Heck reactions

Indexed keywords

ALKADIENE; CODEINE;

ARTICLE; CYCLIZATION; ENZYME SYNTHESIS; HECK REACTION; MITSUNOBU REACTION;

EID: 36549037084     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990833     Document Type: Article

References (27)

1. (a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109.
2. (b) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1956, 78, 1380.
3. For reviews of morphine syntheses, see: (a) Zezula, J.; Hudlicky, T. Synlett 2005, 388.
4. (b) Blakemore, P. R.; White, J. D. Chem. Commun. 2002, 1159.
5. (c) Hudlicky, T.; Reed, J. W.; Mulzer, J.; Trauner, D. Curr. Org. Chem. 2000, 4, 343.
6. (d) Hudlicky, T.; Butora, G.; Fearnley, S.; Gum, A.; Stabile, M. In Studies in Natural Products Chemistry, Vol. 18; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1996, 43-154.
7. Uchida, K.; Yokoshima, S.; Kan, T.; Fukuyama, T. Org. Lett. 2006, 8, 5311.
8. (a) Taber, D. F.; Neubert, T. D.; Rheingold, A. L. J. Am. Chem. Soc. 2002, 124, 12416.
9. (b) Sondergaard, K.; Kristensen, J. L.; Palner, M.; Gillings, N.; Knudsen, G. M.; Roth, B. L.; Begtrup, M. Org. Biomol. Chem. 2005, 3, 4077.
10. (a) Stabile, M. R.; Hudlicky, T.; Meiseis, M. L. Tetrahedron: Asymmetry 1995, 6, 537.
11. (b) For large-scale (15 L) fermentation protocol, see: Endoma, M. A.; Bui, V. P.; Hansen, J.; Hudlicky, T. Org. Process Res. Dev. 2002, 6, 525.
12. (a) Trost, B. M.; Tang, W. J. Am. Chem. Soc. 2002, 124, 14542.
13. (b) Trost, B. M.; Tang, W. J. Am. Chem. Soc. 2005, 127, 14785.
14. (a) Butora, G.; Hudlicky, T.; Fearnley, S. P.; Gum, A. G.; Stabile, M. R.; Abboud, K. A. Tetrahedron Lett. 1996, 37, 8155.
15. (b) Butora, G.; Hudlicky, T.; Fearnley, S. P.; Stabile, M. R.; Gum, A. G.; Gonzalez, D. Synthesis 1998, 665.
16. (a) Frey, D. A.; Duan, C.; Hudlicky, T. Org. Lett. 1999, 1, 2085.
17. (b) Frey, D. A.; Duan, C.; Ghiviriga, I.; Hudlicky, T. Coll. Czech. Chem. Commun. 2000, 65, 561.
18. (a) Parker, K. A.; Fokas, D. J. Am. Chem. Soc. 1992, 114, 9688.
19. (b) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927.
20. (c) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933.
21. (d) Parker, K. A.; Fokas, D. J. Org. Chem. 2006, 71, 449.
22. Nagata, H.; Miyazawa, N.; Ogasawara, K. Chem. Commun. 2001, 1094.
23. Zylstra, G. J.; Gibson, D. T. J. Biol. Chem. 1989, 264, 14940.
24. (a) Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 4021.
25. (b) For experimental procedure, see: Michel, P.; Gennet, D.; Rasat, A. Tetrahedron Lett. 1999, 40, 8575.
26. We are very grateful to Dr. Weiping Tang (University of Wisconsin) for supplying us with detailed description of the experiments performed in Trost's group as well as experimental and spectral information used in monitoring the progress of the reaction. In spite of these details we were never successful in detecting codeine in the reaction mixtures and had to resort to alternative ways of performing the C-9 amination.
27. White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1999, 64, 7871.