The first stereocontrolled synthesis of 12-methylhexahydrobenzo [c]phenanthridine alkaloids

Tetrahedron Asymmetry

Volumn 10, Issue 10, 1999, Pages 1947-1959

  Vicario, Jose L ^a   Badía, Dolores ^a   Domínguez, Esther ^a   Crespo, Ana ^a   Carrillo, Luisa ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

12 METHYLHEXAHYDROBENZO[C]PHENANTHRIDINE; ALKALOID DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHIRALITY; CYCLIZATION; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033591113     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00167-6     Document Type: Article

References (23)

1. (a) Krane, B. D.; Fagbule, M. O.; Shamma, M.; Gözler, B. J. Nat. Prod. 1984, 47, 1.
2. (b) Ninomiya, I.; Naito, T. Recent Developments in the Chemistry of Natural Carbon Compounds; Bognár, R.; Szántay, Cs., Eds.; Akadémiai Kiadó: Budapest, 1984; Vol. 10.
3. Simánek, V. The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, p. 185.
4. (a) Cushman, M.; Mohan, P.; Smith, E. C. R. J. Med. Chem. 1984, 27, 544.
5. (b) Hanaoka, M.; Motegi, A.; Yokumoto, Y. A.; Takahashi, K. JP Patent 02243629, Jpn. Kokai Tokkyo Koho; Chem. Abstr. 1991, 115, 780.
6. (c) Hanaoka, M.; Ekimoto, H.; Kobayashi, F.; Iric, Y.; Takahashi, K. EP Patent 432630, Eur. Pat. Appl.; Chem. Abstr. 1992, 116, 718.
7. (d) Janin, Y. L.; Croisy, A.; Riou, J.-F.; Bisagni, E. J. Med. Chem. 1993, 36, 3686.
8. (a) Cushman, M.; Choong, T.-C.; Valko, J. T.; Koleck, M. P. J. Org. Chem. 1980, 45, 5067.
9. (b) Cheng, R. K. Y; Cheng, C. C. J. Med. Chem. 1978, 21, 199.
10. (c) Cordell, G. A.; Farnsworth, N. R. Heterocycles 1976, 4, 393.
11. Tan, G. T.; Miller, J. F.; Kinghorn, A. D.; Hughes, S. H.; Pezzuto, J. M. Biochem. Biophys. Res. Commun. 1992, 185, 370.
12. Cushman, M.; Moham, P. J. Med. Chem. 1985, 28, 1031.
13. (a) Ninomiya, I.; Yamamoto, O.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1983, 2165.
14. (b) Cushman, M.; Abbaspour, A.; Gupta, Y. P. J. Am. Chem. Soc. 1983, 105, 2873.
15. (c) Cushman, M.; Choong, T.-C.; Valko, J. T.; Koleck, M. P. Tetrahedron Lett. 1980, 21, 3845.
16. (d) Shamma, M.; Tomlinson, H. H. J. Org. Chem. 1978, 43, 2852.
17. (e) Oppolzer, W. Heterocycles 1980, 14, 1615.
18. (f) Iida, H.; Endo, I.; Narimiya, M.; Kikuchi, T. Heterocycles 1980, 14, 1325.
19. Vicario, J. L.; Badía, D.; Domínguez, E.; Carrillo, L. J. Org. Chem. 1999, in press.
20. Sotomayor, N.; Vicente, T.; Domínguez, E.; Lete, E.; Villa, M.-J. Tetrahedron 1994, 50, 2207.
21. Spassov, S. L. Tetrahedron 1971, 27, 1323.
22. For a review on the Pictet-Spengler cyclization see Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
23. For general experimental procedures see Ref. 8.