Related Experiment Video
Updated: Jan 20, 2026
Ozonolysis of Alkenes: Principle and Applications
Published on: April 30, 2023
Diastereoselective Synthesis of Triterpenoid 1,2,4-Trioxolanes by Griesbaum Co-ozonolysis
Oxana B Kazakova1, Elmira F Khusnutdinova1, Anastasiya V Petrova1
1Ufa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences , Ufa , 450054 , Russian Federation.
Abstract:
Diastereoselective synthesis of triterpenoid 1,2,4-trioxolanes by Griesbaum co-ozonolysis was shown for the first time. Ozonolysis of 2-methoxyoximes (syn-anti-isomers mixture) of allobetulin or methyl oleanoate with CF3-ketones resulted in asymmetrical spiro-1,2,4-trioxolanes as mixtures of diastereomers in yields up to 80-85%. The configuration of the spiro-C-2 center of individual ozonides was determined by 2D NMR spectra and X-ray crystallographic analysis. The products of ozonolysis of triterpenoid 3-methoxyoximes were mixtures of regioisomeric N-methoxylactams. Thus, the fundamental differences in the oxidation of homologous triterpenoid 2- or 3-methoxyoximes with ozone have been established. These results may afford a new stage in the development of the Griesbaum method as applied to natural compounds and biologically active peroxides.
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