Ozonolytic Transformations of ( S )-( –)-Limonene and Abietic Acid in the Presence of Pyridine

Controlled ozonolysis of (S)-( –)-limonene in the presence of Py gave 4-methyl-3-(3-oxobutyl)pent-4-enal or 4-methyl-3-(3-oxobutyl)pent-4-enoic acid depending on the solvent (CH2Cl2 or MeOH). Exhaustive ozonolysis produced 3-acetyl-6-oxoheptanoic acid. Ozonolysis of abietic acid in CH2Cl2 in the presence of Py formed stable epoxytrioxolaneabietic acid; in MeOH –Py, the epoxyketoaldehyde corresponding to cleavage of the C13–C14 bond.
Source: Chemistry of Natural Compounds - Category: Chemistry Source Type: research
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