Oxidative transformations of cembrane diterpenoids. VI. Epoxidation of isocembrol
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The stereochemistry of the epoxidation of the diterpene alcohol isocembrol has been studied. The main direction of attack of peracids is the C11 double bond of isocembrol, with the predominant formation of the 11S,12S-epoxide. The ratio of the monoepoxyisocembrols does not change appreciably with a variation in the temperature of the reaction or in the peracid used. 11S,12S-Epoxyisocembrol has been isolated as a natural product from the oleoresin of the Siberian stone pine.
KeywordsDouble Bond Epoxide Sesquiterpene Lactone Peracetic Acid Epoxide Ring
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