Synthesis of (-)-aphanorphine using aryl radical cyclization

Organic Letters

Volumn 3, Issue 16, 2001, Pages 2427-2429

  Tamura, Osamu ^a   Yanagimachi, Takehiko ^a   Kobayashi, Tetsuya ^a   Ishibashi, Hiroyuki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

APHANORPHINE; BRIDGED COMPOUND; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PYRROLE DERIVATIVE;

ARTICLE; CHEMISTRY; CYANOBACTERIUM; CYCLIZATION; SYNTHESIS;

BRIDGED COMPOUNDS; CYANOBACTERIA; CYCLIZATION; INDICATORS AND REAGENTS; PYRROLES;

EID: 0035833714     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015818j     Document Type: Article

References (27)

1. For isolation of 1, see: (a) Gulavita, N.; Hori, A.; Shimizu, Y.; Laszlo, P.; Clardy, J. Tetrahedron Lett. 1988, 29, 4381. For synthesis or synthetic studies of 1, see:
2. (b) Takano, S.; Inomata, K.; Sato, T.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 1591.
3. (c) Takano, S.; Inomata, K.; Sato, T.; Takahashi, M.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1990, 290.
4. (d) Honda, T.; Yamamoto, A.; Cui, Y.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1992, 531.
5. (e) Hulme, A. N.; Henry, S. S.; Meyers, A. I. J. Org. Chem. 1995, 60, 1265.
6. (f) Meyers, A. I.; Schmidt, W.; Santiago, B. Heterocycles 1995, 40, 525.
7. (g) Fadel, A.; Arzel, P. Tetrahedron: Asymmetry 1995, 6, 893.
8. (h) Hallinan, K. O.; Honda, T. Tetrahedron 1995, 51, 12211.
9. (i) Node, M.; Imazato, H.; Kurosaki, R.; Kawano, Y.; Inoue, T.; Nishide, K.; Fuji, K. Heterocycles 1996, 42, 811.
10. (j) Shiotani, S.; Okada, H.; Nakamata, K.; Yamamoto, T.; Sekino, F. Heterocycles 1996, 43, 1031.
11. (k) Fadel, A.; Arzel, P. Tetrahedron: Asymmetry 1997, 8, 371.
12. (l) Shimizu, M.; Kamikubo, T.; Ogasawara, K. Heterocycles 1997, 46, 21.
13. (a) Ishibashi, H.; Kobayashi, T.; Takamasu, D. Synlett 1999, 1286.
14. (b) Ishibashi, H.; Kobayashi, T.; Nakashima, S.; Tamura, O. J. Org. Chem. 2000, 65, 9022.
15. Pal, S.; Mukhopadhyaya, J. K.; Ghatak, U. R. J. Org. Chem. 1994, 59, 2687.
16. Mayer, S. C.; Ramanjulu, J.; Vera, M. D.; Pfizenmayer, A. J.; Joullié, M. M. J. Org. Chem. 1994, 59, 5192.
17. Nagumo, S.; Mizukami, M.; Akutsu, N.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1999, 40, 3209.
18. The stereochemistry of the major isomer 7a was established by three-step transformation into 12 in 57% yield. See ref 5.
19. Grayson, J. I.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1977, 2263.
20. 3, the reaction gave only a trace amount of 10a, probably as a result of facile enolization of ketone 9a.
21. For a review, see: Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: Oxford, 1991; Vol. 1, p 743.
22. 2Li took place.
23. Ghosh, A. K.; Mukhopadhyaya, J. K.; Ghatak, U. R. J. Chem. Soc., Perkin Trans. 1 1997, 2747.
24. Barton, D. H. R.; Motherwell, W. B. Heterocycles 1984, 21, 1. See also: Campbell, J. A.; Rapoport, H. J. Org. Chem. 1996, 61, 6313.
25. Barton, D. H. R.; Motherwell, W. B. Heterocycles 1984, 21, 1. See also: Campbell, J. A.; Rapoport, H. J. Org. Chem. 1996, 61, 6313.
26. For reductive methylation of a secondary amine with Raney nickel in methanol, see: François, D.; Lallemand, M.-C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. Angew. Chem., Int. Ed. 1998, 37, 104. See also: He, X.-S.; Brossi, A. J. Heterocycl. Chem. 1991, 28, 1741.
27. For reductive methylation of a secondary amine with Raney nickel in methanol, see: François, D.; Lallemand, M.-C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. Angew. Chem., Int. Ed. 1998, 37, 104. See also: He, X.-S.; Brossi, A. J. Heterocycl. Chem. 1991, 28, 1741.