Natural cyclic α,β-enone monoterpenoids in nucleophilic addition reactions

Chemistry of Natural Compounds

Volumn 42, Issue 4, 2006, Pages 367-388

  Ishmuratov, G Yu ^a   Kharisov, R Ya ^a   Latypova, E R ^b   Talipov, R F ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b Birsk Branch of Federal State Budgetary Educational Establishment of Higher Education Bashkir State University   (Russian Federation)

Author keywords

1,2 xxx 1,4 addition reactions; Michael reaction; Natural cyclic , enone monoterpenoids; Organometallic reagents

Indexed keywords

EID: 33748998737     PISSN: 00093130     EISSN: 15738388     Source Type: Journal    
DOI: 10.1007/s10600-006-0161-z     Document Type: Article

References (83)

1. R. Ya. Kharisov, R. R. Gazetdinov, O. V. Botsman, R. R. Muslukhov, G. Yu. Ishmuratov, and G. A. Tolstikov, zh. Org. Khim., 36, 1047 (2002).
2. F. A. Valeev and I. P. Tsypysheva, in: Materials of the International Ecological Conference "Service of the Big City," Ufa (1999), 130.
3. M. Alami, S. Marguais, and G. Cahiez, Org. Synth., 72, 135 (1997).
4. B. H. Lipshutz, M. R. Wood, and R. Tirado, Org. Synth., 74, 2525 (1999).
5. O. Pamies, G. Net, A. Ruiz, C. Claver, and S. Woodward, Tetrahedron: Asymmetry, 11, 871 (2000).
6. M. E. Idrissi and M. Santelli, J. Org. Chem., 53, 1010 (1988).
7. G. Neef, S. Baesler, G. Depke, and H. Vierhufe, Tetrahedron Lett., 40, 7969 (1999).
8. O. Takazawa, H. Tamura, K. Kogami, and K. Hayashi, Bull. Chem. Soc. Jpn., 55, 1907 (1982).
9. S. Torii, T. Inokuchi, and R. Oi, J. Org. Chem., 48, 1944 (1983).
10. D. Seyferd, New Applications of Organometallic Reagents in Organic Synthesis, Elsevier, Amsterdam (1976).
11. R. Ya. Kharisov, E. R. Latypova, R. F. Talipov, G. Yu. Ishmuratov, and G. A. Tolstikov, Khim. Prir. Soedin., 396 (2004).
12. S. S. Hall and J. F. McEroe, J. Org. Chem., 40, 271 (1975).
13. S. Kim and Y. C. Moon, Bull. Korean Chem. Soc., 3, 81 (1982).
14. S. P. Tanis, M. C. McMills, and P. M. Herrinton, J. Org. Chem., 50, 5887 (1985).
15. P. Metzner, J. Chem. Soc. Chem. Commun., No. 6, 335 (1982).
16. G. M. Whitesides, W. F. Fischer, J. S. Fillipo, R. W. Bashe, and H. O. House, J. Am. Chem. Soc., 91, 4871 (1969).
17. G. H. Posner, Org. React, 19, 293 (1972).
18. G. H. Posner, Org. React, 22, 107 (1975).
19. C. P. Casey and M. S. Cesa, J. Am. Chem. Soc., 101, 4236 (1979).
20. H. O. House and J. M. Wilkins, J. Org. Chem., 43, 2443 (1978).
21. M. Dagonneau, Bull. Soc. Chim. Fr., No. 7-8, Pt. 2, 269 (1982).
22. E. C. Ashby, J. D. Buhler, I. G. Lopp, T. L. Wieseman, J. S. Bowers, J. T. Laemmle, J. Am. Chem. Soc., 98, 6561 (1976).
23. L. F. Fieser and M. Fieser, Advanced Organic Chemistry, Reinhold Pub. Corp., New York (1961).
24. H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966).
25. E. J. Corey and H. E. Ensley, Synthesis, 12, 749 (1975).
26. H. Buschmann and H. D. Scharf, Synthesis, 10, 827 (1988).
27. H. E. Ensley, C. A. Parnell, and E. J. Corey, J. Org. Chem., 43, 1610 (1978).
28. E. R. Latypova, R. Ya. Kharisov, G. Yu. Ishmuratov, and R. F. Talipov, in: Materials of the Fourth International Conference of Young Scientists "Modern Trends in Organic Synthesis and Chemical Formation Problems," St. Petersburg (2005), 358.
29. G. H. Posner, C. E. Whitten, and J. J. Sterling, J. Am. Chem. Soc., 95, 7788 (1973).
30. B. H. Lipshutz, R. S. Wilhelm, and J. Kozlowski, Tetrahedron Lett., 23, 3755 (1982).
31. R. M. Coates and L. O. Sandefur, J. Org. Chem., 39, 275 (1974).
32. J. P. Marino and J. S. Farina, Tetrahedron Lett., 45, 3901 (1975).
33. K. Yasuhiro, S. Wakita, and K. Natsuki, Tetrahedron Lett., 47, 4577 (1979).
34. G. Cahiez and M. Alami, Tetrahedron Lett., 30, 3541 (1989).
35. W. Tuckmantel, K. Oshima, and H. Nozaki, Chem. Ber., 119, 1581 (1986).
36. L. Bagnell, E. A. Jeffery, A. Meisters, and T. Mole,Aust J. Chem., 28, 801 (1975).
37. Y. Ito, H. Kato, and T. Saegusa, J. Org. Chem., 47, 741 (1982).
38. K. Koga, K. Tomioka, K. Yasuda, and T. Takigawa, Jpn. Pat. No. 60-174535 (1987);
39. Ref. Zh. Khim., 11, 11O5IP (1988).
40. W. G. Dauben and D. M. Michno, J. Org. Chem., 42, 682 (1977).
41. R. Ya. Kharisov, E. R. Latypova, R. F. Talipov, R. R. Muslukhov, G. Yu. Ishmuratov, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 2146 (2003).
42. A. Srikrishna and R. Viswajanani, Tetrahedron Lett., 37, 2863 (1996).
43. A. Srikrishna, J. Santosh, and P. Praveen Kumar, Tetrahedron Lett., 41, 3177 (2000).
44. A. Srikrishna and D. Vijaykumar, Tetrahedron Lett., 39, 4901 (1998).
45. A. Srikrishna and D. Vijaykumar, J. Chem. Soc., Perkin Trans. 1, 2583 (2000).
46. A. Srikrishna, P. Praveen Kumar, and T. Jagadeeswar Reddy, Tetrahedron Lett., 39, 5815 (1998).
47. A. Srikrishna, T. Jagadeeswar Reddy, and P. Praveen Kumar, J. Chem. Soc., Perkin Trans. 1, 3143 (1998).
48. A. Srikrishna, K. Anebouselvy, and T. Jagadeeswar Reddy, Tetrahedron Lett., 41, 6643 (2000).
49. A. Srikrishna and K. Anebouselvy, Tetrahedron Lett., 43, 5261 (2002).
50. A. Srikrishna, V. Sharma, and P. Hemamalini, J. Chem. Soc., Chem. Commun., No. 23, 1681 (1990).
51. A. Srikrishna and P. Hemamalini, Indian J. Chem., Sect. B, 29, 152 (1990).
52. O. P. Vig, M L. Sharma, and S. D. Sethi, Indian J. Chem., Sect. B, 19, 176 (1980).
53. P. Weyerstahl, R. Rilk, and H. Marschall-Weyerstahl, Liebigs Ann. Chem., 89 (1987).
54. C. Alexandre and F. Rouessac, J. Chem. Soc., Chem. Commun., 275 (1975).
55. A. Murai, N. Tanimoto, N. Sakamoto, and T. Masamune, J. Am. Chem. Soc., 110, 1985 (1988).
56. A. Srikrishna, T. J. Reddy, and S. Nagaraju, Tetrahedron Lett., 37, 1679 (1996).
57. A. Srikrishna and T. J. Reddy, J. Chem. Soc., Perkin Trans. 1, 2040 (2001).
58. E. J. Corey, B. C. Pan, D. H. Hua, and D. R. Deardorff, J. Am. Chem. Soc., 104, 6816 (1982).
59. T. M Meulemans, G. A. Stork, B. J. Jansen, and A. De Groot, Tetrahedron Lett., 39, 6565 (1998).
60. T. M Meulemans, G. A. Stork, F. Z. Macaev, B. J. Jansen, and A. De Groot, J. Org. Chem., 64, 9178 (1999).
61. L. H. D. Jenniskens and A. De Groot, Tetrahedron Lett., 38, 7463 (1997).
62. L. H. D. Jenniskens and A. De Groot, Tetrahedron, 54, 5617 (1998).
63. B. J. Jansen, C. J. Hendrikx, N. Masalov, G. A. Stork, T. M. Meulemans, F. Z. Macaev, and A. De Groot, Tetrahedron, 56, 2075 (2000).
64. A. De Groot, B. J. M. Jansen, A. A. Verstegen-Haaksma, H. J. Swarts, R. V. A. Orru, G. A. Stork, and J. B. P. A. Wijnberg, Pure Appl. Chem., 66, 2053 (1994).
65. D. W. Theobald, Tetrahedron, 25, 3139 (1969).
66. P. Ballester, A. Costa, A. G. Raso, A. Gomez-Solivellas, and R. Mestres, J. Chem. Soc., Perkin Trans. 1, 1711 (1988).
67. R. B. Zhao, Y. F. Zhao, G. Q. Song, and Y. L. Wu, Tetrahedron Lett., 31, 3559 (1990).
68. Y.-F. Zhao, R.-B. Zhao, G. Q. Song, and Y. L. Wu, Huaxue Xuebao: Acta Chim. Sin., 52, 823 (1994).
69. A. Srikrishna and P. Ravi Kumar, Tetrahedron Lett., 43, 1109 (2002).
70. A. Srikrishna and T. J. Reddy, J. Chem. Soc., Perkin Trans. 1, 3293 (1997).
71. K. Kaliappan and G. S. R. Suubba Rao, J. Chem. Soc., Perkin Trans. 1, 3387 (1997).
72. A. Srikrishna and S. J. Gharpure, J. Chem. Soc., Perkin Trans. 1, 3191 (2000).
73. S. Maiti, S. Bhaduri, B. Achari, A. K. Banerjee, et al., Tetrahedron Lett., 37, 8061 (1996).
74. B. H. Hagivara, H. Uda, and T. Kodama, J. Chem. Soc., Perkin Trans. 1, 963 (1980).
75. E. R. Latypova, Candidate Dissertation in Chemical Sciences, Inst. Org. Chem., Ufa Sci. Cent., RAS, Ufa (2005).
76. J. Wolinsky and H. S. Hauer, J. Org. Chem., 34, 380 (1969).
77. A. M. Chibiryaev, N. De Kimpe, and A. V. Tkachev, Tetrahedron Lett., 41, 8011 (2000).
78. J. Christoffers, J. Chem. Soc., Perkin Trans. 1, 3141 (1997).
79. K. Shimizu, M. Miyagi, T. Kanno, T. Kodama, and Y. Kitayama, Tetrahedron Lett., 44, 7421 (2003).
80. J.-M. Pons and M. Santelli, Tetrahedron Lett., 23, 4937 (1982).
81. J.-M. Pons and M. Santelli, Tetrahedron, 46, 513 (1990).
82. B. J. Boyer, R. J. P. Corrui, R. Perz, and C. Reye, J. Chem. Soc., Chem. Commun., 122 (1981).
83. M. D. Bachi, Y. V. Bilokin, and A. Melman, Tetrahedron Lett., 39, 3035 (1998).