Aryl radical cyclizations: One-pot syntheses of protoberberine and pavine alkaloids

Organic Letters

Volumn 2, Issue 16, 2000, Pages 2535-2537

  Orito, Kazuhiko ^a   Satoh, Yoshitaka ^a   Nishizawa, Hidetoshi ^a   Harada, Rika ^a   Tokuda, Masao ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BERBERINE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PROTOBERBERINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALKALOIDS; BERBERINE ALKALOIDS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034632415     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006213a     Document Type: Article

References (26)

1. See refs 3 and 12 cited in Matulenko, M. A.; Meyers, A. I. J. Org. Chem. 1996, 61, 573-580.
2. Huffman, J. W.; Miller, E. G. J. Org. Chem. 1960, 25, 90-92.
3. Battersby, A. R.; LeCount, D. J.; Garrant, S.; Thrift, R. I. Tetrahedron 1961, 14, 46-53.
4. Brown, D. B.; Dyke, S. F. Tetrahedron 1966, 22, 2429-2435.
5. Govindachan, T. R.; Nagarajan, K.; Charubala, R.; Pai, R. Ind. J. Chem. 1970, 763-765.
6. Dean, T. R.; Rapoport, H. J. Org. Chem. 1978, 43, 2115-2122, 4183-4189.
7. For a review, see: Banik, B. K. Curr. Org. Chem. 1999, 3, 469-486.
8. Orito, K.; Uchiito, S.; Satoh, Y.; Tatsuzawa, T.; Harada, R.; Tokuda, M. Org. Lett. 2000, 2, 307-310.
9. It has been reported that the acid-catalyzed cyclization of 6,7-dimethoxy isocarbostylril 1 (X = O) failed to give 3d (ref 4), and (±)-8-oxosinactine (3c) was obtained in a low yield (ref 5).
10. Orito, K.; Miyazawa, M.; Kanbayashi, R.; Tokuda, M.; Suginome, H. J. Org. Chem. 1999, 64, 6583-6596, and references cited therein.
11. Kuivila, H. G. Synthesis 1970, 499-4509.
12. Yamaguchi, R., Hanasaki, T.; Uchimoto, K. Chem. Lett. 1988, 913-916.
13. Beckwith, A. L.; Westwood, S. W. Tetrahedron Lett. 1989, 45, 5269-5272.
14. Gözler, B. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1987; Vol. 31, pp 317-389.
15. Anderson, O. Liebigs Ann. 1854, 95, 235-240.
16. (a) Pyman, F. I.; Reynolds, W. C. J. Chem. Soc. 1910, 97, 1320-1328.
17. (b) Battersby, A. R.; Binks, R. J. Chem. Soc. 1955, 2888-2896.
18. Stermitz, F. R.; Lwo, S.-Y.; Kallos, G. J. Am. Chem. Soc. 1963, 85, 1551-1552
19. Rice, K. C.; Ripka, W. C; Reden, J.; Brossi, A. J. Org. Chem. 1980, 45, 601-607.
20. (e) Nomoto, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1982, 1113-1115.
21. Baker, A. C.; Battersby, A. R. J. Chem. Soc. C 1967, 1317-1323.
22. For the synthesis of protoberberine alkaloids by radical cyclization, see: (a) Takano, S.; Suzuki, M.; Ogasawara, K. Heterocycles 1990, 31, 1151-1156.
23. (b) Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315-2318.
24. Dai-Ho, G.; Mariano, P. S. J. Org. Chem. 1998, 52, 704-707.
25. Nimgirawath, S.; Ronghousabury, O.-A. Aust. J. Chem. 1994, 47, 951-955.
26. (e) Ishibashi, S.; Kawakami, H.; Nakagawa, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1997, 2291-2295.