Products of the ozonolysis of epitorulosol

The structure of the products of the ozonization of epitorulosol 13S-labda-8(20),14-diene-13,19-diol] (I) has been established. Compound (I) (1 g) was ozonized at –30°C in 100 ml of absolute CH₃OH until saturation. The O₃ was driven off by nitrogen, 1 ml of (CH₃)₂S was added at –10°C, and the mixture was stirred for 1 h each at –10, 0, and 20°C and was worked up, and the product (1.13 g) was chromatographed on a column containing 45 g of silica gel. The following were eluted in the order of increasing polarity: 420 mg of 19-hydroxy-8,13;8,14-diepoxy-13S-15,20-bisnorlabdan-14-one (II), mp 141.5–142.5°C (from petroleum ether), ] _D ²³ –63° (c 3.1); 255 mg of 8,13;8,14-diepoxy-13S-15,20-bisnorlabdane-14,19-diol (III), characterized in the form of the diacetate (IV) with mp 100–107°C (from petroleum ether); and 117 mg of 19-hydroxy-14,15,20-trisnorlabdane-8,13-dione (V), mp 82–83°C from petroleum ether-diethyl ether (1:1)], ] _D ²⁶ –40° (c 1.7). The same products but in different ratios were formed on the ozonization of (I) in CH₂Cl₂-Py or in hexane followed by decomposition of the ozonide by heating with H₂O. The ]_D values were measured in CHCl₃. Details of the IR and PMR spectra are given.Institute of Chemistry, Academy of Sciences of the Moldavian SSR, Kishinev. Institute of Organic Chemistry, Siberian Branch of the USSR Academy of Sciences, Novosibirsk. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 524–527, July–August, 1987.