Cycloaromatization of enediyne model compounds via a reaction cascade triggered by hydrolysis of the α-alkynylmalonates

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 865-868

  Shibuya, Masayuki ^a   Wakayama, Masakazu ^a   Naoe, Yoshimitsu ^a   Kawakami, Tadaaki ^a   Ishigaki, Katsuya ^a   Nemoto, Hisao ^a   Shimizu, Hisashi ^a   Nagao, Yoshimitsu ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; MALONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030066058     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02285-6     Document Type: Article

References (24)

1. A. G. Myers, E. Y. Kuo, and N. S. Finney, J. Am. Chem. Soc., 111, 8057 (1989); R. Nagata, H. Yamanaka, E. Okazaki, and I. Saito, Tetrahedron Lett., 30, 4995 (1989).
2. A. G. Myers, E. Y. Kuo, and N. S. Finney, J. Am. Chem. Soc., 111, 8057 (1989); R. Nagata, H. Yamanaka, E. Okazaki, and I. Saito, Tetrahedron Lett., 30, 4995 (1989).
3. N. Ishida, K. Miyazaki, K. Kumagai, and M. Rikimaru, J. Antibiot., Ser.A 18, 68 (1965); K. Edo, M. Mizugaki, Y. Koide, H. Seto, K. Furihata, N. Otake, and, N. Ishida, Tetrahedron Lett., 26, 331 (1985); M. Shibuya, K. Toyooka, and S. Kubota, Tetrahedron Lett., 25, 1171 (1984).
4. N. Ishida, K. Miyazaki, K. Kumagai, and M. Rikimaru, J. Antibiot., Ser.A 18, 68 (1965); K. Edo, M. Mizugaki, Y. Koide, H. Seto, K. Furihata, N. Otake, and, N. Ishida, Tetrahedron Lett., 26, 331 (1985); M. Shibuya, K. Toyooka, and S. Kubota, Tetrahedron Lett., 25, 1171 (1984).
5. N. Ishida, K. Miyazaki, K. Kumagai, and M. Rikimaru, J. Antibiot., Ser.A 18, 68 (1965); K. Edo, M. Mizugaki, Y. Koide, H. Seto, K. Furihata, N. Otake, and, N. Ishida, Tetrahedron Lett., 26, 331 (1985); M. Shibuya, K. Toyooka, and S. Kubota, Tetrahedron Lett., 25, 1171 (1984).
6. Review; K. C. Nicolaou, A. L. Smith, and E. W. Yue, Proc. Natl. Acad. Sci. USA, 90, 5881 (1993).
7. A. G. Myers, and P. S. Dragovich, J. Am. Chem. Soc., 111, 9130 (1989); K. C. Nicolaou, P. Maligres, J. Shin, E. de Leon, and D. Rideout, J. Am. Chem. Soc., 112, 7825 (1990).
8. A. G. Myers, and P. S. Dragovich, J. Am. Chem. Soc., 111, 9130 (1989); K. C. Nicolaou, P. Maligres, J. Shin, E. de Leon, and D. Rideout, J. Am. Chem. Soc., 112, 7825 (1990).
9. Y. Nagao, K. Kim, S. Sano, H. Kakegawa, W. S. Lee, H. Shimizu, M. Shiro, and N. Katunuma, Tetrahedron Lett., preceding paper.
10. M. Shibuya, Y. Sakai, and Y. Naoe, Tetrahedron Lett., 36, 897 (1995).
11. S. F. Martin and B. Benage, Tetrahedron Lett., 25, 4863 (1984).
12. 6 with diethyl ketomalonate, followed by methylation.
13. Several examples of homolytic intramolecular 1,5-hydrogen atom shift have been reported in the field of enediyne chemistry. See, D.-H. Chin and I. H. Goldberg, J. Am. Chem. Soc., 114, 1914 (1992); P. A. Wender and M. J. Tebbe, Tetrahedron, 50, 1419 (1994); H. Audrain, T. Skrydstrup, G. Ulibarri, C. Riche, A. Chiaroni, and D. S. Grierson, Tetrahedron, 50, 1469 (1994); S. Kawata, T. Oishi, and M. Hirama, Tetrahedron Lett., 35, 4595 (1994); Z. Wang and K. K. Wang, J. Org. Chem., 59, 4738 (1994).
14. Several examples of homolytic intramolecular 1,5-hydrogen atom shift have been reported in the field of enediyne chemistry. See, D.-H. Chin and I. H. Goldberg, J. Am. Chem. Soc., 114, 1914 (1992); P. A. Wender and M. J. Tebbe, Tetrahedron, 50, 1419 (1994); H. Audrain, T. Skrydstrup, G. Ulibarri, C. Riche, A. Chiaroni, and D. S. Grierson, Tetrahedron, 50, 1469 (1994); S. Kawata, T. Oishi, and M. Hirama, Tetrahedron Lett., 35, 4595 (1994); Z. Wang and K. K. Wang, J. Org. Chem., 59, 4738 (1994).
15. Several examples of homolytic intramolecular 1,5-hydrogen atom shift have been reported in the field of enediyne chemistry. See, D.-H. Chin and I. H. Goldberg, J. Am. Chem. Soc., 114, 1914 (1992); P. A. Wender and M. J. Tebbe, Tetrahedron, 50, 1419 (1994); H. Audrain, T. Skrydstrup, G. Ulibarri, C. Riche, A. Chiaroni, and D. S. Grierson, Tetrahedron, 50, 1469 (1994); S. Kawata, T. Oishi, and M. Hirama, Tetrahedron Lett., 35, 4595 (1994); Z. Wang and K. K. Wang, J. Org. Chem., 59, 4738 (1994).
16. Several examples of homolytic intramolecular 1,5-hydrogen atom shift have been reported in the field of enediyne chemistry. See, D.-H. Chin and I. H. Goldberg, J. Am. Chem. Soc., 114, 1914 (1992); P. A. Wender and M. J. Tebbe, Tetrahedron, 50, 1419 (1994); H. Audrain, T. Skrydstrup, G. Ulibarri, C. Riche, A. Chiaroni, and D. S. Grierson, Tetrahedron, 50, 1469 (1994); S. Kawata, T. Oishi, and M. Hirama, Tetrahedron Lett., 35, 4595 (1994); Z. Wang and K. K. Wang, J. Org. Chem., 59, 4738 (1994).
17. Several examples of homolytic intramolecular 1,5-hydrogen atom shift have been reported in the field of enediyne chemistry. See, D.-H. Chin and I. H. Goldberg, J. Am. Chem. Soc., 114, 1914 (1992); P. A. Wender and M. J. Tebbe, Tetrahedron, 50, 1419 (1994); H. Audrain, T. Skrydstrup, G. Ulibarri, C. Riche, A. Chiaroni, and D. S. Grierson, Tetrahedron, 50, 1469 (1994); S. Kawata, T. Oishi, and M. Hirama, Tetrahedron Lett., 35, 4595 (1994); Z. Wang and K. K. Wang, J. Org. Chem., 59, 4738 (1994).
18. 6 using dideuterio phthalide (96.5% deuterium contents at the benzylic position) as a starting material.
19. 1H NMR.
20. It is well established that homolytic hydrogen abstraction from EtOH is conducted from C-H bond exclusively, but not from O-H bond; e.g., F. Fontana, F. Minisci, Y. M. Yan, and L. Zhao, Tetrahedron Lett., 34, 2517 (1993).
21. Possibilities of intermolecular or intramolecular disproportionation of biradicals leading to zwitterionic intermediate have been suggested; H. Sugiyama, K. Yamashita, M. Nishi, and I. Saito, Tetrahedron Lett., 33, 515 (1992); A. G. Myers, P. S. Dragovich, and E. Y. Kuo, J. Am. Chem. Soc., 114, 9369 (1992); N. J. Turro, A. Evenzahav, and K. C. Nicolaou, Tetrahedron Lett., 35, 8089 (1994).
22. Possibilities of intermolecular or intramolecular disproportionation of biradicals leading to zwitterionic intermediate have been suggested; H. Sugiyama, K. Yamashita, M. Nishi, and I. Saito, Tetrahedron Lett., 33, 515 (1992); A. G. Myers, P. S. Dragovich, and E. Y. Kuo, J. Am. Chem. Soc., 114, 9369 (1992); N. J. Turro, A. Evenzahav, and K. C. Nicolaou, Tetrahedron Lett., 35, 8089 (1994).
23. Possibilities of intermolecular or intramolecular disproportionation of biradicals leading to zwitterionic intermediate have been suggested; H. Sugiyama, K. Yamashita, M. Nishi, and I. Saito, Tetrahedron Lett., 33, 515 (1992); A. G. Myers, P. S. Dragovich, and E. Y. Kuo, J. Am. Chem. Soc., 114, 9369 (1992); N. J. Turro, A. Evenzahav, and K. C. Nicolaou, Tetrahedron Lett., 35, 8089 (1994).
24. 3): 1.26 (3H, t, J=7.1), 3.42 (3H, s), 3.47 (3H, s), 4.19 (1H, dq, J=10.7, 7.1), 4.28 (1H, dq, J=10.7 and 7.1) 4.73 (2H, s), 4.73 (1H, d, J=12.7), 4.92 (1H, d, J=12.7), 5.17 (1H, s), 7.43-7.69 (6H, m), 8.04 (1H, d, J=8.4), and 9.99 (1H, s).