Efficient construction of cyclopenta[b]quinoline core of isoschizozygane alkaloids via intramolecular formal hetero-Diels-Alder reaction

Organic Letters

Volumn 5, Issue 14, 2003, Pages 2509-2512

  Magomedov, Nabi A ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKALOID; CYCLOPENTA[B]QUINOLINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; POLYMERIZATION; STEREOCHEMISTRY;

EID: 0141854284     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034776r     Document Type: Article

References (24)

1. Renner, U.; Kernweisz, P. Experientia 1963, 19, 244-246.
2. Renner, U. Lloydia 1964, 27, 406-415.
3. Hajiček, J.; Taimr, J.; Budešinsky, M. Tetrahedron Lett. 1998, 39, 505-508.
4. Kariba, R. M.; Houghton, P. J.; Yenesew, A. J. Nat. Prod. 2002, 65, 566-569.
5. Povarov, L. S.; Mikhailov, B. M. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1963, 955-956. For a review, see: Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656-670.
6. Povarov, L. S.; Mikhailov, B. M. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1963, 955-956. For a review, see: Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656-670.
7. (a) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267-270.
8. (b) Cheng, Y.-S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 50, 5678-5686.
9. (c) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3386-3395.
10. (d) Grieco, P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855-5858.
11. (e) Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039-1053.
12. (f) Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51, 6115-6132.
13. (g) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977-8978.
14. (h) Pearson, W. H.; Fang, W.-K. Isr. J. Chem. 1997, 37, 39-46.
15. (i) Crousse, B.; Begue, J.-P.; Bonnet-Delpon, D. J. Org. Chem. 2000, 65, 5009-5013.
16. (j) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 3, 1973-1976.
17. (k) Powell, D. A.; Batey, R. A. Org. Lett. 2002, 4, 2913-2916.
18. (l) Cheng, D.; Zhou, J.; Saiah, E.; Beaton, G. Org. Lett. 2002, 4, 4411-4414.
19. The only example of construction of cyclopentaquinoline ring system by intramolecular reaction of aryl imine with olefin was reported by Tietze: Wölfling, J.; Frank, E.; Schneider, G.; Tietze, L. F. Eur. J. Org. Chem. 1999, 3013-3020. For the synthesis of octahydroacridine derivatives see: Laschat, S.; Lauterwein, J. J. Org. Chem. 1993, 58, 2856-2861.
20. The only example of construction of cyclopentaquinoline ring system by intramolecular reaction of aryl imine with olefin was reported by Tietze: Wölfling, J.; Frank, E.; Schneider, G.; Tietze, L. F. Eur. J. Org. Chem. 1999, 3013-3020. For the synthesis of octahydroacridine derivatives see: Laschat, S.; Lauterwein, J. J. Org. Chem. 1993, 58, 2856-2861.
21. Nucleophilicity parameters N for trans-olefin and monosubstituted conjugated diene are -2.45 and 1.49, respectively: Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77.
22. Commercially available from Alfa Aesar.
23. Reaction also yields 11% of the corresponding 1,2,3-substituted arene.
24. PM3 geometry optimization was conducted using Spartan SGI Version 5.1.1.