Abstract
Using (2E)-4,4-dimethoxy-2-butenal as starting compound, methods were developed for synthesis of (2E,4E)- and (2E,4Z)-dimethoxyalkadienes. Deacetalization of the latter gives with high yield the corresponding dienals which are naturally occurring compounds and also synthons for preparation of conjugated dienes as key compounds for building up other natural products.
Similar content being viewed by others
REFERENCES
Gree, R., Tourbah, H., and Carrie, R., Tetrahedron Lett., 1986, vol. 27, no. 41, pp. 4983-4986; Meyers, A.I. and Brinkmeyer, R.S., Tetrahedron Lett., 1975, no. 21, pp. 1749-1752.
Khrimyan, A.P., Ovanesyan, A.L., Streinz, L., Svatos, A., Khrimyan, E.P., Makaryan, G.M., and Badanyan, Sh.O., Zh. Bioorg. Khim., 1992, vol. 18, no. 7, pp. 969-978.
Khrimian, A.P., Ovanessian, A.L., Streinz, L., Svatos, A., Romanuk, M., and Badanian, Sh.H., Proc. Conf. on Insecticide Chemistry and Ecology, Tabor, 1990, pp. 137-140.
Ideses, R. and Shani, A., Tetrahedron, 1989, vol. 45, no. 11, pp. 3523-3534.
Naff, F., Decorzant, R., Thommen, W., Willhalm, B., and Ohloff, G., Helv. Chim. Acta, 1975, vol. 58, nos. 109–110, pp. 1016-1037.
Ohloff, G. and Pawlak, M., Helv. Chim. Acta, 1973, vol. 56, no. 3, pp. 1176-1179.
Li Han-Dong, Deng Jan-Neng, Xu Han-Sbeog, Iao Li, and Qu Hai-Sheng, Chin. J. Org. Chem., 1988, vol. 8, no. 2, pp. 167-168.
Kovalev, B.G., Rastegaeva, V.M., Kurts, A.L., and Bundel', Yu.G., Zh. Org. Khim., 1986, vol. 22, no. 9, pp. 1818-1824.
Christmann, K.F., Synthesis, 1969, no. 1, pp. 38-39.
Viola, A. and MacMillan, J.H., J. Am. Chem. Soc., 1970, vol. 92, no. 8, pp. 2404-2410.
Ingham, S., Turner, R.W., and Wallace, T.W., J. Chem. Soc., Chem. Commun., 1985, no. 23, pp. 1664-1666.
Renold, W., Naf-Muller, R., Keller, U., Wilhalm, B., and Ohloff, G., Helv. Chim. Acta, 1974, vol. 57, no. 144, pp. 1301-1308.
Naf, F. and Decorzant, R., Helv. Chim. Acta, 1974, vol. 57, no. 145, pp. 1309-1317.
Goldbach, M., Jakel, E., and Schneider, M.P., J. Chem. Soc., Chem. Commun., 1987, no. 19, pp. 1434-1435.
Tsuboi, S., Masuda, T., and Takedo, A., J. Org. Chem., 1982, vol. 47, no. 23, pp. 4478-4482.
Nakahara, M., Takano, R., Ito, H., Yano, H., Hirase, S., and Harimaya, K., J. Agric. Chem. Soc. Jpn., 1988, vol. 62, no. 2, pp. 157-159; Ref. Zh., Khim., 1989, no. 6E379.
Hara, T., Kubota, E., and Horita, H., J. Agric. Chem. Soc. Jpn., 1987, vol. 61, no. 4, pp. 471-473; Ref. Zh., Khim., 1988, no. 14R436.
Einhorn, J., Beauvais, J., Gallois, M., Descoins, Ch., and Chausse, R., C.R. Acad. Sci., 1984, vol. 299, no. 19, pp. 773-778.
Takeoka, E.R., Flath, R.A., Mon, T.R., Teranishi, R., and Euenert, M., J. Agric. Food Chem., 1990, vol. 38, no. 2, pp. 471-477; Ref. Zh., Khim., 1990, no. 20E16.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Badanyan, S.O., Makaryan, G.M., Ovanesyan, A.L. et al. (2E)-4,4-Dimethoxy-2-butenal in the Synthesis of Conjugated Dienes and Dienals. Russian Journal of Organic Chemistry 37, 633–639 (2001). https://doi.org/10.1023/A:1012479213224
Issue Date:
DOI: https://doi.org/10.1023/A:1012479213224