Abstract
Catalytic hydrogenation of 3-chloro-2-(2,6-dioxopiperidin- 4-ylacetyl)-2-cyclohexenones over palladium catalyst leads to formation of dehydrocycloheximide derivatives. Reduction of the same compounds with Zn-Ag yields dehydroinactone derivatives.
Similar content being viewed by others
REFERENCES
Whiffen, A.J., Bohonas, N., and Emerson, R.L., J. Bacteriol., 1946, vol. 52, no. 4, pp. 610-616.
Preud'Homme, J. and Dubost, M., Handbook of 14th Int. Congr. on Pure and Applied Chemistry, Zurich, 1955, p. 382.
Johnson, F., Starkovsky, N.A., Paton, A.C., and Carlson, A.A., J. Am. Chem. Soc., 1966, vol. 88, no. 1, pp. 149-159.
Lakhvich, F.A., Buravskaya, T.N., and Akhrem, A.A., Khim. Prirodn. Soedin., 1993, no. 4, pp. 598-601.
Buravskaya, T.N. and Lakhvich, F.A., Russ. J. Org. Chem., 1996, vol. 32, no. 7, pp. 969-975; Buravskaya, T.N. and Lakhvich, F.A., Russ. J. Org. Chem., 1998, vol. 34, no. 2, pp. 2503252.
Garmaise, D.L., Chu, D.T.W., Bernstein, E., and Inaba, M., J. Med. Chem., 1979, vol. 22, no. 5, pp. 559-564; Lakhvich, F.A. and Khlebnikova, T.S., Vestsi Akad. Navuk Belarusi, Ser. Khim. Navuk, 1996, no. 4, pp. 101-119.
Lakhvich, F.A., Lis, L.G., Rubinov, D.B., Rubinova, I.L., Kurbako, V.Z., and Bykhovets, A.I., Vestsi Akad. Navuk BSSR, Ser. Khim. Navuk, 1989, no. 1, pp. 51-58; Rubinov, D.B., Rubinova, I.L., and Akhrem, A.A., Chem. Rev., 1999, vol. 99, no. 4, pp. 1047-1065.
Smith, H., J. Chem. Soc., 1953, no. 3, pp. 803-810.
Akhrem, A.A., Lakhvich, F.A., Budai, S.I., Khlebnikova, T.S., and Shcherbakova, T.N., Dokl. Akad. Nauk SSSR, 1976, vol. 226, no. 6, pp. 1326-1329.
Jones, R.A. and Stokes, M.J., Tetrahedron, 1984, vol. 40, no. 6, pp. 1051-1060.
Lakhvich, F.A., Buravskaya, T.N., and Akhrem, A.A., Vestsi Akad. Nauk Belarusi, Ser. Khim. Navuk, 1992, no. 2, pp. 77-83.
Akhrem, A.A., Lakhvich, F.A., and Pyrko, A.N., Zh. Org. Khim., 1983, vol. 19, no. 11, pp. 2322-2328; Clark, R.D. and Heathcock, C.H., J. Org. Chem., 1976, vol. 41, no. 4, pp. 636-643.
Novak, L., Baan, G., Marasfalvi, J., and Szantay, Cs., Chem. Ber., 1980, vol. 113, no. 9, pp. 2939-2949.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Buravskaya, T.N., Lakhvich, F.A. Synthesis of Dehydro Derivatives of Cycloheximide and Inactone. Russian Journal of Organic Chemistry 37, 724–728 (2001). https://doi.org/10.1023/A:1012586621401
Issue Date:
DOI: https://doi.org/10.1023/A:1012586621401