Intramolecular Cyclization of 4-[3-(Trimethylsilyl)prop-1-en-1-yI]-cyclohexanecarbaldehyde with Loss of Formyl Carbon

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 7, 1998, Pages 1639-1647

  Kuroda, Chiaki ^a   Murase, Atsushi ^a   Suzuki, Hideyuki ^a   Endo, Toru ^a   Anzai, Shuzo ^a  

^a RIKKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008174305     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.1639     Document Type: Article

References (29)

1. A. Hosomi, Acc. Chem. Res., 21, 200 (1988).
2. a) G. Majetich, in "Organic Synthesis: Theory and Application," ed by T. Hudlicky, JAI Press, Greenwich (1989), Vol. 1, p. 173;
3. b) D. Schinzer, Synthesis, 1988, 263.
4. For review regarding synthesis of various carbocycles, see: a) T.-L. Ho, "Carbocycle Construction in Terpene Synthesis," VCH, New York (1988); b) C. Thebtaranonth and Y. Thebtaranonth, "Cyclization Reactions," CRC Press, Boca Raton (1994).
5. For review regarding synthesis of various carbocycles, see: a) T.-L. Ho, "Carbocycle Construction in Terpene Synthesis," VCH, New York (1988); b) C. Thebtaranonth and Y. Thebtaranonth, "Cyclization Reactions," CRC Press, Boca Raton (1994).
6. For examples, see: a) G. Majetich, J. -S. Song, A. J. Leigh, and S. M. Condon, J. Org. Chem., 58, 1030 (1993); b) G. Majetich, D. Lowery, V. Khetani, J. -S. Song, K. Hull, and C. Ringold, J. Org. Chem., 56, 3988 (1991).
7. For examples, see: a) G. Majetich, J. -S. Song, A. J. Leigh, and S. M. Condon, J. Org. Chem., 58, 1030 (1993); b) G. Majetich, D. Lowery, V. Khetani, J. -S. Song, K. Hull, and C. Ringold, J. Org. Chem., 56, 3988 (1991).
8. a) C. Kuroda, S. Shimizu, and J. Y. Satoh, J. Chem. Soc., Chem. Commun., 1987, 286; J. Chem. Soc., Perkin Trans. 1, 1990, 519;
9. a) C. Kuroda, S. Shimizu, and J. Y. Satoh, J. Chem. Soc., Chem. Commun., 1987, 286; J. Chem. Soc., Perkin Trans. 1, 1990, 519;
10. b) C. Kuroda, S. Shimizu, T. Haishima, and J. Y. Satoh, Bull. Chem. Soc. Jpn., 66, 2298 (1993);
11. c) C. Kuroda, S. Inoue, S. Kato, and J. Y. Satoh, J. Chem. Res. (S), 1993, 62;
12. d) C. Kuroda, S. Inoue, R. Takemura, and J. Y. Satoh, J. Chem. Soc., Perkin Trans. 1, 1994, 521;
13. e) C. Kuroda and K. Ito, Bull. Chem. Soc. Jpn., 69, 2297 (1996).
14. a) C. Kuroda, Y. Ohnishi, and J. Y. Satoh, Tetrahedron Lett., 34, 2613 (1993);
15. b) C. Kuroda, H. Nogami, Y. Ohnishi, Y. Kimura, and J. Y. Satoh, Tetrahedron, 53, 839 (1997).
16. a) C. Kuroda and Y. Hirono, Tetrahedron Lett., 35, 6895 (1994);
17. b) C. Kuroda, H. Sumiya, A. Murase, and A. Koito, J. Chem. Soc., Chem. Commun., 1997, 1177.
18. a) S. E. Denmark and E. J. Weber, Helv. Chim. Acta, 66, 1655 (1983);
19. b) S. E. Denmark and N. G. Almstead, J. Org. Chem., 59, 5130 (1994);
20. c) S. E. Denmark, B. R. Henke, and E. Weber, J. Am. Chem. Soc., 109, 2512 (1987).
21. For more examples, see: a) D. Schinzer, C. Allagiannis, and S. Wichmann, Tetrahedron, 44, 3851 (1988); b) K. Nishitani, Y Nakamura, R. Orii, C. Arai, and K. Yamakawa, Chem. Pharm. Bull., 41, 822 (1993).
22. For more examples, see: a) D. Schinzer, C. Allagiannis, and S. Wichmann, Tetrahedron, 44, 3851 (1988); b) K. Nishitani, Y Nakamura, R. Orii, C. Arai, and K. Yamakawa, Chem. Pharm. Bull., 41, 822 (1993).
23. a) G. Majetich, K. Hull, and R. Desmond, Tetrahedron Lett., 26, 2751 (1985);
24. b) G. Majetich, K. Hull, J. Defauw, and T. Shawe, Tetrahedron Lett., 26, 2755 (1985).
25. I. Fleming and I. Paterson, Synthesis, 1979, 446.
26. 1,4-Cyclohexanedimethanol is commercially available as a mixture of cis- and trans-isomers (14a and 14b).
27. a) V. V. Rheenen, Tetrahedron Lett., 1969, 985;
28. b) W. Sucrow, Chem. Ber., 100, 259 (1967).
29. C. Kuroda and K. Ito, J. Chem. Res. (S), 1995, 270.