An efficient synthetic method for β-cyclolavandulal and its corresponding alcohol

Recueil des Travaux Chimiques des Pays-Bas-Journal of the Royal Netherlands

Volumn 115, Issue 10, 1996, Pages 438-440

  Oda, Mitsunori ^a   Isobe, Atsushi ^a   Hayashi, Masashi ^a   Miyatake, Ryuta ^a   Shimao, Ichiro ^a   Kuroda, Shigeyasu ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33645490831     PISSN: 01650513     EISSN: None     Source Type: Journal    
DOI: 10.1002/recl.19961151005     Document Type: Article

References (21)

1. Trivial names are used for naturally occurring compounds and ones closely related to them in this paper. IUPAC names are as follows: 1: 2,4,4-trimethylcyclohex-1-enecarbaldehyde; 2: 2,4,4-trimethylcyclohex-1-enecarboxylicacid; 4: 2,4,4-trimethylcyclohex-1-enemethanol 6: methyl 2,4,4-trimethylcyclohex-1-enecarboxylate.
2. M.K. Logani, I.P. Varshney, R.C. Pandey and S. Dev, Tetrahedron Lett. 2645 (1967).
3. S.M. Dixit, A.S. Rao and S.K. Paknikar, Chem. and Ind. 1256 (1967).
4. A. Brenner and H. Schinz, Helv. Chim. Acta 35, 1615 (1952).
5. R.B. Bates, D.J. Eckert, S.K. Paknikar and V.P. Thalacker, Tetrahedron Lett. 3811 (1972).
6. S. Imai, K. Furihata, Y. Hayakawa, T. Noguchi and H. Seto, J. Antibiot. 42, 1196(1989).
7. 7a O. Nakayama, M. Yagi, M. Tanaka, S. Kiyoto, M. Okuhara and M. Kohsaka, J. Antibiot. 42, 1221 (1989);
8. b O. Nakayama, N. Shigematsu, A. Katayama, S. Takase, S. Kiyoto, M. Hashimoto and M. Kohsaka, J. Antibiot. 42, 1230 (1989).
9. M. Matsumoto and H. Seto, J. Antibiot. 44, 1471 (1991).
10. T. Kitahara, Y. Kinoshita, S. Aono, M. Miyake, T. Hasegawa, H. Watanabe and K. Mori, Pure Appl. Chem. 66, 2083 (1994).
11. Y. Kinoshita, H. Watanabe, T. Kitahara and K. Mori, Synlett 186 (1995).
12. A. Brenner and U. Schinz, Helv. Chim. Acta 35, 1333 (1952).
13. A. Brenner, U. Steiner and H. Schinz, Helv. Chim. Acta 35, 1336 (1952).
14. For other approaches to 1 or 4, see Refs. 4, 5, 10, 11 and 12.
15. The same sequence was reported to apply to cyclohexanone; J.P. Freeman, "Organic Syntheses Coll. Vol. VII", M. Alderdice, F.W. Sum and L. Weiler, John Wiley & Sons, Inc., N.Y., 1990, p351.
16. U. Steiner and H. Schinz, Helv. Chim. Acta 34, 1508 (1951).
17. F.W. Sun, L. Wieler, Can. J. Chem. 57, 1431 (1979).
18. J. Herscoviti and K. Antonakis, J. Chem. Soc., Chem. Commun. 561 (1980).
19. T. Kimura, M. Fujita, and T. Ando, Chemistry Lett. 1387 (1987).
20. E.J. Corey and C.U. Kim, J. Am. Chem. Soc. 94, 7586 (1972).
21. G. Büchi, O. Jeger and L. Ruzicka, Helv. Chim. Acta 31, 241 (1948).