Synthesis and Antifungal Activity of Pinane Alcohols and Acids.

A simple and efficient synthesis of cis- and trans-myrtanic acids in preparative yields of 54–58% and 72–74%, respectively, was proposed and consisted of oxidation of cis- and trans-myrtanols by CrO3–AcOH upon addition of the oxidant to a solution of the starting alcohols at room temperature. Tests of the obtained compounds for antifungal activity showed lower activity for the quaternary salts than for the starting acids and greater efficacy for the cis-isomers than for the trans-isomers. However, the alcohols themselves, i.e., cis- and trans-myrtanols and (–)-myrtenol, had the greatest activities. [ABSTRACT FROM AUTHOR]