Authors: P F Vlad A N Aryku M N Koltsa É N Shmidt V A Pentegova
Publish Date: 1987/07/01
Volume: 23, Issue: 4, Pages: 436-438
Abstract
The structure of the products of the ozonization of epitorulosol 13Slabda82014diene1319diol 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 CH32S 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 113 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 19hydroxy813814diepoxy13S1520bisnorlabdan14one II mp 1415–1425°C from petroleum ether α D 23 −63° c 31 255 mg of 813814diepoxy13S1520bisnorlabdane1419diol III characterized in the form of the diacetate IV with mp 100–107°C from petroleum ether and 117 mg of 19hydroxy141520trisnorlabdane813dione V mp 82–83°C from petroleum etherdiethyl ether 11 α D 26 −40° c 17 The same products but in different ratios were formed on the ozonization of I in CH2Cl2Py or in hexane followed by decomposition of the ozonide by heating with H2O The αD values were measured in CHCl3 Details of the IR and PMR spectra are givenInstitute 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
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