A simple and efficient synthetic route to chiral isopavines. Synthesis of (-)-O-methylthalisopavine and (-)-amurensinine

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 6716-6721

  Carrillo, Luisa ^a   Badía, Dolores ^a   Domínguez, Esther ^a   Vicario, José L ^a   Tellitu, Imanol ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMURENSININE; ISOPAVINE; ISOQUINOLINE DERIVATIVE; NATURAL PRODUCT; O METHYLTHALISOPAVINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS;

EID: 0030847794     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9708102     Document Type: Article

References (28)

1. See, for example: (a) Tellitu, I.; Badía, D.; Domínguez, E.; Carrillo, L. Heterocycles 1996, 43, 2099-2112. (b) Badía, D.; Domínguez, E.; Tellitu, I. Tetrahedron 1992, 48, 4419-4430.
2. See, for example: (a) Tellitu, I.; Badía, D.; Domínguez, E.; Carrillo, L. Heterocycles 1996, 43, 2099-2112. (b) Badía, D.; Domínguez, E.; Tellitu, I. Tetrahedron 1992, 48, 4419-4430.
3. For pharmacological activities, see: (a) Weber, E.; Keana, J.; Barmettler, P. PCT Int. Appl. WO 12575, 1990; Chem. Abstr. 1991, 115, 106019w. (b) Childers, W. E., Jr.; Abou-Gharbia, M. A. U.S. Patent 4940789, 1990; Chem. Abstr, 1990, 113, 191190w.
4. For pharmacological activities, see: (a) Weber, E.; Keana, J.; Barmettler, P. PCT Int. Appl. WO 12575, 1990; Chem. Abstr. 1991, 115, 106019w. (b) Childers, W. E., Jr.; Abou-Gharbia, M. A. U.S. Patent 4940789, 1990; Chem. Abstr, 1990, 113, 191190w.
5. For pharmacological activities, see: (a) Weber, E.; Keana, J.; Barmettler, P. PCT Int. Appl. WO 12575, 1990; Chem. Abstr. 1991, 115, 106019w. (b) Childers, W. E., Jr.; Abou-Gharbia, M. A. U.S. Patent 4940789, 1990; Chem. Abstr, 1990, 113, 191190w.
6. For pharmacological activities, see: (a) Weber, E.; Keana, J.; Barmettler, P. PCT Int. Appl. WO 12575, 1990; Chem. Abstr. 1991, 115, 106019w. (b) Childers, W. E., Jr.; Abou-Gharbia, M. A. U.S. Patent 4940789, 1990; Chem. Abstr, 1990, 113, 191190w.
7. For syntheses of natural and non-natural isopavines, see, for example: (a) Gözler, B. In The Alkaloids; Academic Press: New York, 1987; Vol. 31, pp 342-355. (b) Yasuda, M.; Hamasuna, S.; Yamano, K.; Kubo, J.; Shima, K. Heterocycles 1992, 34, 965-977. (c) Kametani, T.; Higashiyama, K.; Honda, T. Chem. Pharm. Bull 1984, 32, 1614-1618 (d) Jung, M. E.; Miller, S. J. J. Am. Chem. Soc. 1981, 103, 1984-1992. (e) Dyke, S. F.; Kinsman, R. G.; Warren, P.; White, A. W .C. Tetrahedron 1978, 34, 241-245. (f) Dyke, S. F.; ; Ellis, A. C.; Kinsman, R. G.; White, A. W .C. Tetrahedron 1974, 30, 1193-1199. (g) Rice, K. C.; Ripka, W. C.; Reden, J.; Brossi, A. J. Org. Chem. 1980, 45, 601-607.
8. For syntheses of natural and non-natural isopavines, see, for example: (a) Gözler, B. In The Alkaloids; Academic Press: New York, 1987; Vol. 31, pp 342-355. (b) Yasuda, M.; Hamasuna, S.; Yamano, K.; Kubo, J.; Shima, K. Heterocycles 1992, 34, 965-977. (c) Kametani, T.; Higashiyama, K.; Honda, T. Chem. Pharm. Bull 1984, 32, 1614-1618 (d) Jung, M. E.; Miller, S. J. J. Am. Chem. Soc. 1981, 103, 1984-1992. (e) Dyke, S. F.; Kinsman, R. G.; Warren, P.; White, A. W .C. Tetrahedron 1978, 34, 241-245. (f) Dyke, S. F.; ; Ellis, A. C.; Kinsman, R. G.; White, A. W .C. Tetrahedron 1974, 30, 1193-1199. (g) Rice, K. C.; Ripka, W. C.; Reden, J.; Brossi, A. J. Org. Chem. 1980, 45, 601-607.
9. For syntheses of natural and non-natural isopavines, see, for example: (a) Gözler, B. In The Alkaloids; Academic Press: New York, 1987; Vol. 31, pp 342-355. (b) Yasuda, M.; Hamasuna, S.; Yamano, K.; Kubo, J.; Shima, K. Heterocycles 1992, 34, 965-977. (c) Kametani, T.; Higashiyama, K.; Honda, T. Chem. Pharm. Bull 1984, 32, 1614-1618 (d) Jung, M. E.; Miller, S. J. J. Am. Chem. Soc. 1981, 103, 1984-1992. (e) Dyke, S. F.; Kinsman, R. G.; Warren, P.; White, A. W .C. Tetrahedron 1978, 34, 241-245. (f) Dyke, S. F.; ; Ellis, A. C.; Kinsman, R. G.; White, A. W .C. Tetrahedron 1974, 30, 1193-1199. (g) Rice, K. C.; Ripka, W. C.; Reden, J.; Brossi, A. J. Org. Chem. 1980, 45, 601-607.
10. For syntheses of natural and non-natural isopavines, see, for example: (a) Gözler, B. In The Alkaloids; Academic Press: New York, 1987; Vol. 31, pp 342-355. (b) Yasuda, M.; Hamasuna, S.; Yamano, K.; Kubo, J.; Shima, K. Heterocycles 1992, 34, 965-977. (c) Kametani, T.; Higashiyama, K.; Honda, T. Chem. Pharm. Bull 1984, 32, 1614-1618 (d) Jung, M. E.; Miller, S. J. J. Am. Chem. Soc. 1981, 103, 1984-1992. (e) Dyke, S. F.; Kinsman, R. G.; Warren, P.; White, A. W .C. Tetrahedron 1978, 34, 241-245. (f) Dyke, S. F.; ; Ellis, A. C.; Kinsman, R. G.; White, A. W .C. Tetrahedron 1974, 30, 1193-1199. (g) Rice, K. C.; Ripka, W. C.; Reden, J.; Brossi, A. J. Org. Chem. 1980, 45, 601-607.
11. For syntheses of natural and non-natural isopavines, see, for example: (a) Gözler, B. In The Alkaloids; Academic Press: New York, 1987; Vol. 31, pp 342-355. (b) Yasuda, M.; Hamasuna, S.; Yamano, K.; Kubo, J.; Shima, K. Heterocycles 1992, 34, 965-977. (c) Kametani, T.; Higashiyama, K.; Honda, T. Chem. Pharm. Bull 1984, 32, 1614-1618 (d) Jung, M. E.; Miller, S. J. J. Am. Chem. Soc. 1981, 103, 1984-1992. (e) Dyke, S. F.; Kinsman, R. G.; Warren, P.; White, A. W .C. Tetrahedron 1978, 34, 241-245. (f) Dyke, S. F.; ; Ellis, A. C.; Kinsman, R. G.; White, A. W .C. Tetrahedron 1974, 30, 1193-1199. (g) Rice, K. C.; Ripka, W. C.; Reden, J.; Brossi, A. J. Org. Chem. 1980, 45, 601-607.
12. For syntheses of natural and non-natural isopavines, see, for example: (a) Gözler, B. In The Alkaloids; Academic Press: New York, 1987; Vol. 31, pp 342-355. (b) Yasuda, M.; Hamasuna, S.; Yamano, K.; Kubo, J.; Shima, K. Heterocycles 1992, 34, 965-977. (c) Kametani, T.; Higashiyama, K.; Honda, T. Chem. Pharm. Bull 1984, 32, 1614-1618 (d) Jung, M. E.; Miller, S. J. J. Am. Chem. Soc. 1981, 103, 1984-1992. (e) Dyke, S. F.; Kinsman, R. G.; Warren, P.; White, A. W .C. Tetrahedron 1978, 34, 241-245. (f) Dyke, S. F.; ; Ellis, A. C.; Kinsman, R. G.; White, A. W .C. Tetrahedron 1974, 30, 1193-1199. (g) Rice, K. C.; Ripka, W. C.; Reden, J.; Brossi, A. J. Org. Chem. 1980, 45, 601-607.
13. For syntheses of natural and non-natural isopavines, see, for example: (a) Gözler, B. In The Alkaloids; Academic Press: New York, 1987; Vol. 31, pp 342-355. (b) Yasuda, M.; Hamasuna, S.; Yamano, K.; Kubo, J.; Shima, K. Heterocycles 1992, 34, 965-977. (c) Kametani, T.; Higashiyama, K.; Honda, T. Chem. Pharm. Bull 1984, 32, 1614-1618 (d) Jung, M. E.; Miller, S. J. J. Am. Chem. Soc. 1981, 103, 1984-1992. (e) Dyke, S. F.; Kinsman, R. G.; Warren, P.; White, A. W .C. Tetrahedron 1978, 34, 241-245. (f) Dyke, S. F.; ; Ellis, A. C.; Kinsman, R. G.; White, A. W .C. Tetrahedron 1974, 30, 1193-1199. (g) Rice, K. C.; Ripka, W. C.; Reden, J.; Brossi, A. J. Org. Chem. 1980, 45, 601-607.
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27. See refs 3b, 3c, and 13.
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