The reaction of alantolactone, a sesquiterpene α,β-unsaturated lactone, with H-phosphonium or H-arsonium triflates proceeds as P–H or As–H addition at the terminal =CH2 moiety to afford novel triphenyl(sesquiterpenyl)phosponium or -arsonium triflates. Their diastereoisomerism at the formed C11 chiral center has been simulated by quantum chemical calculations.

The reaction of the R-pulegone with P–H-phosphonium salts gives the corresponding 8-phosphonio-p-menthan-3-one salts with high regio- and stereoselectivity. The structure of salts was determined by NMR and IR spectroscopy, mass spectrometry and X-ray diffraction analysis.

A convenient approach to the synthesis of 3,3,6-trimethyl-2-chlorocyclohexeno[1,2-d]-1,2-oxaphosphol-3-ene-2-oxide was developed based on the reaction of the naturally occurring terpenoketone pulegone with methyl dichlorophosphite. Treatment of oxaphospholene-2-oxide with water or ethanol yielded γ-phosphoryl ketones, dimephosphone analogs. The studied hydrolysis and alcoholysis processes differ in stereoselectivity.