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 (CH 2 Cl 2 or MeOH). Exhaustive ozonolysis produced 3-acetyl-6-oxoheptanoic acid. Ozonolysis of abietic acid in CH 2 Cl 2 in th...

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Bibliographic Details
Published in:Chemistry of natural compounds 2019-05, Vol.55 (3), p.474-477
Main Authors: Myasoedova, Yu. V., Garifullina, L. R., Nurieva, E. R., Kravchenko, A. A., Ishmuratov, G. Yu
Format: Article
Language:English
Subjects:
Acids
Alkenes
Bonds (Securities)
Dichloromethane
Medicine
Organic Chemistry
Pharmacy
Plant Sciences
Pyridine
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Summary: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 (CH 2 Cl 2 or MeOH). Exhaustive ozonolysis produced 3-acetyl-6-oxoheptanoic acid. Ozonolysis of abietic acid in CH 2 Cl 2 in the presence of Py formed stable epoxytrioxolaneabietic acid; in MeOH–Py, the epoxyketoaldehyde corresponding to cleavage of the C13–C14 bond.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-019-02718-3