Photochemical hydroxymethylation of protoberberine alkaloids. Total synthesis of (±)-solidaline

Tetrahedron Letters

Volumn 37, Issue 20, 1996, Pages 3575-3578

  Suau, Rafael ^a   Nájera, Francisco ^a   Rico, Rodrigo ^a  

^a UNIVERSITY OF MÁLAGA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; SOLIDALINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 17544396622     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00625-9     Document Type: Article

References (24)

1. Southon, I. W.; Buckingham, J. Dictionary of Alkaloids; Chapman and Hall: London; 1989.
2. Lundström, J. Simple Isoquinoline Alkaloids. In The Alkaloids; Brossi, A. Ed.; Academic Press, Inc.:New York, 1983; Vol. 21; Chap. 6; pp. 255-327.
3. Krane, B. D.; Fagbule, M. O.; Shamma, M.; Gözler, B. J. Nat. Prod. 1984, 47, 1-43.
4. Suau, R.; Silva, M. V.; Valpuesta, M. Tetrahedron 1990, 46, 4421-4428.
5. Manske, R. H. F.; Rodrigo, R.; Holland, H. L.; Hughes, D. W.; MacLean, D. B.; Saunders, J. K. Can. J. Chem. 1978, 56, 383-386.
6. Zhang, G. L.; Pan, W. E.; Peng, S. L.; Chen, L.; Chen, W. X., Yaoxue Xuebao 1990, 25, 604. C. A. 1991, 114, 160667y.
7. Zhang, G. L.; Pan, W. E.; Peng, S. L.; Chen, L.; Chen, W. X., Yaoxue Xuebao 1990, 25, 604. C. A. 1991, 114, 160667y.
8. Beecher, C. W. W.; Kelleher, W. J. The Biosynthesis of the Protoberberine Alkaloids. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W. Ed.; Wiley-Interscience: New York; 1988; Vol. 6; Chap. 4; pp. 297-337.
9. Bhakuni, D. S.; Jain, S. Protoberberine Alkaloids. In The Alkaloids; Brossi, A. Ed.; Academic Press, Inc.:New York, 1986; Vol. 28; Chap. 2; pp. 95-181.
10. a) Shamma, M. The Isoquinoline Alkaloids; Academic Press: New York; 1972, Chap. 16, pp. 268-314.
11. b) Hanaoka, M. Transformation Reactions of Protoberberine Alkaloids. In The Alkaloids; Brossi, A. Ed.; Academic Press, Inc.:New York, 1988; Vol. 33; Chap. 3; pp. 141-230.
12. Corey, E. J.; Eckrich, T. M. Tetrahedron Lett. 1983, 24, 3165-3168.
13. Beak, P.; McKinnie, B. G. J. Am. Chem. Soc. 1977, 99, 5213.
14. Seebach, D.; Meyer, N.; Angew. Chem. Int. Ed. Engl. 1976, 15, 438.
15. Tamao, K.; Ishida, N. Tetrahedron Lett. 1984, 25, 4245-4248.
16. a) Padwa, A. Chem. Rev. 1977, 77, 37-68;
17. b) Mariano, P. S. Tetrahedron 1983, 39, 3845-3879;
18. c) Mariano, P. S. The Photochemistry of Substances Containing the C = N Moiety with Emphasis on Electron Transfer Processes. In Organic Photochemistry; Padwa, A. Ed.; Marcel Dekker, Inc.: New York, 1987; Vol. 9, Chap. 1, pp. 1-128.
19. Ishii, H.; Ishikawa, T.; Hosoya, K.; Takao, N. Chem. Pharm. Bull. 1978, 26, 166-170.
20. Satisfactory analytical and spectroscopic data were obtained for all the new compounds.
21. Berberine chloride (2a) was obtained from Aldrich. Palmatine chloride (2b) was extracted from Enantia chloratha: Jalander, L.; Sjöholm, R.; Virtanen, P. Collect. Czech. Chem. Commun. 1990, 55, 2095-2099. 13-methylberberine (2c) and dehydrocorydaline (2d) were prepared from 2a and 2b respectively: Kiparissides, Z.; Fichtner, R. H.; Poplawski, J.; Nalliah, B. C.; MacLean, D. B. Can. J. Chem. 1980, 58, 2770-2779.
22. Berberine chloride (2a) was obtained from Aldrich. Palmatine chloride (2b) was extracted from Enantia chloratha: Jalander, L.; Sjöholm, R.; Virtanen, P. Collect. Czech. Chem. Commun. 1990, 55, 2095-2099. 13-methylberberine (2c) and dehydrocorydaline (2d) were prepared from 2a and 2b respectively: Kiparissides, Z.; Fichtner, R. H.; Poplawski, J.; Nalliah, B. C.; MacLean, D. B. Can. J. Chem. 1980, 58, 2770-2779.
23. Similar hydroxylation of 7-methyl-6,6a-dehydronoraporphines to the corresponding 7-hydroxy-7-methyl-6,6a-dehydronoraporphines was recently reported. Atanes, N.; Pérez, S.; Guitián, E.; Castedo, L.; Saá, J. M. Tetrahedron 1994, 38, 11257-11266.
24. Shamma, M.; Moniot, J. L. Isoquinoline Alkaloids Research. 1972-1977. Plenum Press: New York, 1978; Chap. 19, pp. 254-255.