Diterpene chemistry. II. The preferential oxidation of the vinyl groups of pimaric and sandaracopimaric acids

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Abstract
The use of the Lemieux – von Rudloff technique for the oxidation of the vinyl groups of pimaric (Ib) and sandaracopimaric (IIb) acid methyl esters has been investigated. Although the process leads to the expected C-13 acid V in the case of methyl sandaracopimarate, an unexpected epoxy acid was obtained from methyl pimarate. This product was shown to be the 8β,14β-epoxy-13-α-ketoacid VIIIa, probably arising from an intramolecular process during oxidation of the vinyl group.

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