Synthetic Studies With Pinus Elliottiis' Rosin Derivatives. Oxidation Of Maleopimaric Anhydride Methyl Ester And Trimethyl Fumaropimarate

Ozonolysis of maleopimaric anhydride methyl ester in the presence of tetracyanoethylene led to an epoxide and an ozonide. Ozonolysis of the trimethyl fumaropimarate, followed by treatment with Me2S, led to an epoxide, a diene, a keto-acid and an allylic oxidation product. Some of the compounds obtained were active against Staphylococcus aureus, Bacillus subtilis and Micrococcus luteus.1115963Seebacher, W., Hüfner, A., Haslingeer, E., Weis, R., (1995) Monatsh. Chem., 129, p. 697. , and references cited thereinKsabati, M.B., Schimtz, F.J., (1987) J. Org. Chem., 52, p. 3766Miyamoto, T., Sakamoto, K., Arao, K., Komori, T., Higuchi, R., Sasaki, T., (1996) Tetrahedron, 52, p. 8187Zalkow, L.H., Ford, R.A., Kutney, J.P., (1962) J. Org. Chem., 27, p. 3535Zalkow, L.H., Brannon, D.R., (1964) J. Org. Chem., 29, p. 1296Zalkow, L.H., Girotra, N.N., (1963) J. Org. Chem., 28, p. 2033Zalkow, L.H., Kulkarni, M.V., Girotra, N.N., (1965) J. Org. Chem., 30, p. 1679Halbrook, N.J., Lawrence, R.V., Dressler, R.L., Blackstone, R.C., Herz, W., (1964) J. Org. Chem., 29, p. 1017Santos, C., Rosso, C.R.S., Imamura, P., (1999) M. Synth. Commun., 29, p. 1903Bailey, P.S., (1978) Ozonization in Organic Chemistry, 1. , Academic Press, New YorkHerz, W., Blackstone, R.C., (1969) Atmos Environ, 34, p. 1257Atmos Environ, p. 135Masaki, Y., Miura, T., Ochiai, M., (1996) Bull. Chem. Soc. Jpn., 69, p. 195. , and references cited thereinThe ozonide could be stored in a freezer without decomposition at -5°C for few weeksShiojima, K., Masuda, K., Ageta, K., (1990) Chem. Pharm. Bull., 38, p. 79Li, T., Yang, Y., Li, Y., (1993) J. Chem. Res. (S), p. 30Carlsen, P.H.J., Katsuki, T., Martin, V.S., Sharpless, K.B., (1981) J. Org. Chem., 46, p. 3936Funk, R.L., Abelman, M.M., (1986) J. Org. Chem., 51, p. 3247For convenience, the numbering of carbons for 14 was used the same given for 3Sam, D.J., Simmons, H.F., (1972) J. Am. Chem. Soc., 94, p. 4024Ferreira, J.T.B., Cruz, W.O., Vieira, P.C., Yonashiro, M., (1987) J. Org. Chem., 52, p. 3698Mitra, R.B., Muljiani, Z., Deshmukh, A.R.A., (1982) S. Synth. Commun., 12, p. 1063Aristoff, P.A., Johnson, P.D., Harrison, A.W., (1985) J. Am. Chem. Soc., 107, p. 7961Homans, A.L., Fuchs, A., (1970) J. Chromatogr., 75, p. 327Hamburger, M.O., Cordell, G.A., (1987) J. Nat. Prod., 50, p. 19Bruch, M.K., (1991) Methods of Testing Antiseptics: Antimicrobials Used Topically in Humans and Procedures for Hand Scrubs, in Disinfection, Sterilization and Preservation, 4th. Ed., , Lea & Febinger, PhiladelphiaHalbrook, N.J., Lawrence, R.V., (1958) J. Am. Chem. Soc., 80, p. 36