Total synthesis of (±)-desoxycodeine-D: A novel route to the morphine skeleton

Tetrahedron Letters

Volumn 41, Issue 6, 2000, Pages 915-918

  Liou, Jing Ping ^a   Cheng, Chen Yu ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

Alkaloids; Analgesics; Palladium; Palladium compounds; Rearrangements

Indexed keywords

ALKALOID DERIVATIVE; DESOXYCODEINE D; ISOVANILLIN; MORPHINE; PALLADIUM COMPLEX; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DRUG STRUCTURE; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0034606984     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02188-7     Document Type: Article

References (23)

1. For reviews on the total synthesis of morphine alkaloids, see: (a) Hudlicky, T.; Butora, G.; Fearnley, S. P.; Gum, A. G.; Stabile, M. R. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1996; pp. 43-154. (b) Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp. 357-369. (c) Szántay, G.; Dörnyei, G. In The Alkaloids; Cordell, G. A.; Brossi, A., Eds.; Academic Press: New York, 1994; Vol. 45, p. 127 ff.
2. For reviews on the total synthesis of morphine alkaloids, see: (a) Hudlicky, T.; Butora, G.; Fearnley, S. P.; Gum, A. G.; Stabile, M. R. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1996; pp. 43-154. (b) Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp. 357-369. (c) Szántay, G.; Dörnyei, G. In The Alkaloids; Cordell, G. A.; Brossi, A., Eds.; Academic Press: New York, 1994; Vol. 45, p. 127 ff.
3. For reviews on the total synthesis of morphine alkaloids, see: (a) Hudlicky, T.; Butora, G.; Fearnley, S. P.; Gum, A. G.; Stabile, M. R. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1996; pp. 43-154. (b) Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp. 357-369. (c) Szántay, G.; Dörnyei, G. In The Alkaloids; Cordell, G. A.; Brossi, A., Eds.; Academic Press: New York, 1994; Vol. 45, p. 127 ff.
4. For more recent studies on the total synthesis of morphine, see: (a) Parsons, P. J.; Penkett, C. S.; Shell, A. Chem. Rev. 1996, 96, 195-206. (b) Butora, G.; Hudlicky, T.; Fearnley, S. P.; Gum, A. G.; Stabile, M. R.; Abboud, K. Tetrahedron Lett. 1996, 37, 8155-8158. (c) Mulzer, J.; Dürner, G.; Trauner, D. Angew. Chem., Int. Ed. Engl. 1996, 35, 2830-2832. (d) Mulzer, J.; Bats, J. W.; List, B.; Opatz, T.; Trauner, D. Synlett 1997, 441-444. (e) White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1997, 62, 5250-5251. (f) Trauner, D.; Bats, J. W.; Werner, A.; Mulzer, J. J. Org. Chem. 1998, 63, 5908-5918.
5. For more recent studies on the total synthesis of morphine, see: (a) Parsons, P. J.; Penkett, C. S.; Shell, A. Chem. Rev. 1996, 96, 195-206. (b) Butora, G.; Hudlicky, T.; Fearnley, S. P.; Gum, A. G.; Stabile, M. R.; Abboud, K. Tetrahedron Lett. 1996, 37, 8155-8158. (c) Mulzer, J.; Dürner, G.; Trauner, D. Angew. Chem., Int. Ed. Engl. 1996, 35, 2830-2832. (d) Mulzer, J.; Bats, J. W.; List, B.; Opatz, T.; Trauner, D. Synlett 1997, 441-444. (e) White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1997, 62, 5250-5251. (f) Trauner, D.; Bats, J. W.; Werner, A.; Mulzer, J. J. Org. Chem. 1998, 63, 5908-5918.
6. For more recent studies on the total synthesis of morphine, see: (a) Parsons, P. J.; Penkett, C. S.; Shell, A. Chem. Rev. 1996, 96, 195-206. (b) Butora, G.; Hudlicky, T.; Fearnley, S. P.; Gum, A. G.; Stabile, M. R.; Abboud, K. Tetrahedron Lett. 1996, 37, 8155-8158. (c) Mulzer, J.; Dürner, G.; Trauner, D. Angew. Chem., Int. Ed. Engl. 1996, 35, 2830-2832. (d) Mulzer, J.; Bats, J. W.; List, B.; Opatz, T.; Trauner, D. Synlett 1997, 441-444. (e) White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1997, 62, 5250-5251. (f) Trauner, D.; Bats, J. W.; Werner, A.; Mulzer, J. J. Org. Chem. 1998, 63, 5908-5918.
7. For more recent studies on the total synthesis of morphine, see: (a) Parsons, P. J.; Penkett, C. S.; Shell, A. Chem. Rev. 1996, 96, 195-206. (b) Butora, G.; Hudlicky, T.; Fearnley, S. P.; Gum, A. G.; Stabile, M. R.; Abboud, K. Tetrahedron Lett. 1996, 37, 8155-8158. (c) Mulzer, J.; Dürner, G.; Trauner, D. Angew. Chem., Int. Ed. Engl. 1996, 35, 2830-2832. (d) Mulzer, J.; Bats, J. W.; List, B.; Opatz, T.; Trauner, D. Synlett 1997, 441-444. (e) White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1997, 62, 5250-5251. (f) Trauner, D.; Bats, J. W.; Werner, A.; Mulzer, J. J. Org. Chem. 1998, 63, 5908-5918.
8. For more recent studies on the total synthesis of morphine, see: (a) Parsons, P. J.; Penkett, C. S.; Shell, A. Chem. Rev. 1996, 96, 195-206. (b) Butora, G.; Hudlicky, T.; Fearnley, S. P.; Gum, A. G.; Stabile, M. R.; Abboud, K. Tetrahedron Lett. 1996, 37, 8155-8158. (c) Mulzer, J.; Dürner, G.; Trauner, D. Angew. Chem., Int. Ed. Engl. 1996, 35, 2830-2832. (d) Mulzer, J.; Bats, J. W.; List, B.; Opatz, T.; Trauner, D. Synlett 1997, 441-444. (e) White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1997, 62, 5250-5251. (f) Trauner, D.; Bats, J. W.; Werner, A.; Mulzer, J. J. Org. Chem. 1998, 63, 5908-5918.
9. For more recent studies on the total synthesis of morphine, see: (a) Parsons, P. J.; Penkett, C. S.; Shell, A. Chem. Rev. 1996, 96, 195-206. (b) Butora, G.; Hudlicky, T.; Fearnley, S. P.; Gum, A. G.; Stabile, M. R.; Abboud, K. Tetrahedron Lett. 1996, 37, 8155-8158. (c) Mulzer, J.; Dürner, G.; Trauner, D. Angew. Chem., Int. Ed. Engl. 1996, 35, 2830-2832. (d) Mulzer, J.; Bats, J. W.; List, B.; Opatz, T.; Trauner, D. Synlett 1997, 441-444. (e) White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1997, 62, 5250-5251. (f) Trauner, D.; Bats, J. W.; Werner, A.; Mulzer, J. J. Org. Chem. 1998, 63, 5908-5918.
10. Cheng, C. Y.; Liou, J. P.; Lee, M. J. Tetrahedron Lett. 1997, 38, 4571-4574.
11. Small, L. F.; Mallone, J. E. J. Org. Chem. 1940, 5, 350-354.
12. Cheng, C. Y.; Hsin, L. W.; Liou, J. P. Tetrahedron 1996, 52, 10935-10944.
13. Boyd, D. R.; Davies, R. J. H.; Hamilton, L.; McCullough, J. J. J. Chem. Soc., Perkin Trans. 1 1992, 31-35.
14. 13C, IR, and mass spectrometric analysis. Chemical yields refer to isolated, purified products.
15. Hazlet, S. E.; Brotherton, R. J. J. Org. Chem. 1962, 27, 3253-3256.
16. Mitsunobu, O. Synthesis 1981, 1-28.
17. Wu, G. Z.; Lamaty, F.; Negishi, E. I. J. Org. Chem. 1989, 54, 2507-2508.
18. (a) Kametani, T.; Kobari, T.; Fukumoto, K.; Fujihara, M. J. Chem. Soc. C 1971, 1796-1800.
19. (b) Ito, K.; Furukawa, H.; Iida, T.; Lee, K. H.; Soine, T. O. J. Chem. Soc., Chem. Commun. 1974, 1037-1038.
20. (c) Kametani, T.; Huang, S. P.; Ujiie, A.; Ihara, M.; Fukumoto, K. Heterocycles 1976, 4, 1223-1228.
21. (d) Kametani, T.; Ujiie, A.; Huang, S. P.; Ihara, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1977, 394-397.
22. (e) Kametani, T.; Huang, S. P.; Koseki, C.; Ihara, M.; Fukumoto, K. J. Org. Chem. 1977, 42, 3040-3046.
23. 1H NMR data is in agreement with that reported in the literature. See: Kshirsagar, T. A.; Portoghese, P. S. J. Org. Chem. 1998, 63, 1706-1708.