Oxidative transformations of cembrane diterpenoids. VI. Epoxidation of isocembrol

descriptionPublicationkeyboard_double_arrow_right Article 01 Sep 1983 English Publisher:Springer Science and Business Media LLCJournal:Chemistry of Natural Compounds, volume 19, pages 546-551 (issn: 0009-3130, eissn: 1573-8388,

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Authors: V. A. Raldugin; N. I. Yaroshenko; V. I. Mamatyuk;

doi: 10.1007/bf00576080

Oxidative transformations of cembrane diterpenoids. VI. Epoxidation of isocembrol

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Abstract

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.

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