First Stereoselective [4 + 2] Cycloaddition Reactions of 3-Cyanochromone Derivatives with Electron-Rich Dienes: An Approach to the ABC Tricyclic Frame of Arisugacin

Journal of Organic Chemistry

Volumn 62, Issue 23, 1997, Pages 7904-7905

  Hsung, Richard P ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000554446     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971479p     Document Type: Article

References (25)

1. The preliminary results of this work were carried out at Columbia University.
2. For isolation of arisugacin see: (a) Omura, S.; Kuno, F.; Otoguro, K.; Sunazuka, T.; Shiomi, K.; Masuma, R.; Iwai, Y. J. Antibiot. 1995, 48, 745.
3. For biological activities of arisugacin see: (b) Kuno, F.; Otoguro, K.; Shiomi, K.; Iwai, Y.; Omura, S. J. Antibiot. 1996, 49, 742. Kuno, F.; Shiomi, K.; Otoguro, K.; Sunazuka, T.; Omura, S. J. Antibiot. 1996, 49, 748.
4. For biological activities of arisugacin see: (b) Kuno, F.; Otoguro, K.; Shiomi, K.; Iwai, Y.; Omura, S. J. Antibiot. 1996, 49, 742. Kuno, F.; Shiomi, K.; Otoguro, K.; Sunazuka, T.; Omura, S. J. Antibiot. 1996, 49, 748.
5. (a) Tomoda, H.; Tabata, N.; Yang, D. J.; Namatame, I.; Tanaka, H.; Omura, S.; Kaneko, T. J. Antibiot. 1996, 49, 292.
6. (b) Smith, A. B., III; Kinsho, T.; Sunazuka, T.; Omura, S. Tetrahedron Lett. 1996, 6461.
7. (a) Corey, E. J.; Jardine, P. D. S.; Rohloff, J. C. J. Am. Chem. Soc. 1988, 110, 3672.
8. (b) Ziegler, F. E.; Jaynes, B. H.; Saindane, M. T. Ibid. 1987, 109, 8115.
9. (a) Alzheimer, A. Gesamte Psych. 1907, 64, 1264. Arisugacin's therapeutic potential was found on the basis of the cholinergic hypothesis since it is a potent inhibitor of acetylcholine esterase (AChE).
10. For a leading reference see: (b) Jaén, J. C.; Gregor, V. E.; Lee, C.; Davis, R.; Emmerling, M. Bioorg. Med. Chem. Lett. 1996, 6, 737.
11. For a leading reference on another potent inhibitor huperzine see: (c) Kozikowski, A. P.; Ding, Q. J.; Saxena, A.; Doctor, B. P. Bioorg. Med. Chem. Lett. 1996, 6, 259.
12. (a) Cremins, P. J.; Saengchantara, S. T.; Wallace, T. W. Tetrahedron 1987, 13, 3075.
13. (b) Ohkata, K.; Kubo, T.; Miyamoto, K.; Ono, M.; Yamamoto, J.; Akiba, K. Heterocycles 1994, 38, 1483.
14. (a) Groundwater, P. W.; Hibbs, D. E.; Hursthouse, M. B.; Nyerges, M. J. Chem. Soc., Perkin Trans. 1 1997, 163.
15. (b) Chen, D.; Totah, N. I. Abstracts of Papers, 213th National Meeting of the American Chemical Society, San Francisco, CA, Spring 1997; American Chemical Society: Washington, DC, 1997; ORGN-173.
16. 3-Cyano-4H-benzopyran-4-thione was reported to give xanthione upon reacting with 1-(dimethylamino)-1,3-butadiene. An initial [4 + 2] cycloadduct, albeit never isolated, was postulated as the intermediate involved in providing xanthione after dehydroamination and dehydrocyanation. See: Sain, B.; Prajapati, D.; Mahajan, A. R.; Sandhu, J. S. Bull. Soc. Chim. Fr. 1994, 131, 313.
17. Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Chanlland, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293.
18. NOE enhancement was observed only for the tertiary allylic hydrogen on the newly formed ring upon irradiation of the β-hydrogen on the γ-pyrone ring in endo-7, whereas NOE enhancement was observed only for methyl hydrogens upon irradiation of the same β-hydrogen in exo-7.
19. Gammill, R. B. Synthesis 1979, 901.
20. Stork, G.; Hsung, R. P. Unpublished results.
21. 3(vinyl)Sn and 2,2,6-trimethyl-1-cyclohexenetriflate in THF at 65°C. For a reference see: Scott, W. J.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630.
22. For leading references see: (a) Engler, T. A.; Sampath, U.-S.; Vander Velde, D.; Takusagawa, F. Synth. Commun. 1992, 22, 2031. (b) Engler, T. A.; Sampath, U.-S.; Vander Velde, D.; Takusagawa, F. Tetrahedron 1992, 48, 9399.
23. For leading references see: (a) Engler, T. A.; Sampath, U.-S.; Vander Velde, D.; Takusagawa, F. Synth. Commun. 1992, 22, 2031. (b) Engler, T. A.; Sampath, U.-S.; Vander Velde, D.; Takusagawa, F. Tetrahedron 1992, 48, 9399.
24. For some examples see: (a) Brieger, G. Tetrahedron Lett. 1965, 4429. (b) He, J.-F.; Wu, Y.-L. Tetrahedron 1988, 44, 1933.
25. For some examples see: (a) Brieger, G. Tetrahedron Lett. 1965, 4429. (b) He, J.-F.; Wu, Y.-L. Tetrahedron 1988, 44, 1933.