It signals mating readiness, particularly attracting females who are also in the receptive phase of their sexual cycle.
[3] Unlike many pheromones in bark beetles, which are derived from terpenes present in host plants, frontalin does not follow this pathway.
The resulting hydroxy group can then be reacted with the Cornforth reagent (pyridinium dichromate), followed by the addition of a Grignard compound derived from 5-bromo-2-methylpent-1-ene.
[1] An alternative synthetic route begins with a Diels-Alder reaction between 3-buten-2-one and methacrylic acid methyl ester.
Oxymercuration with mercury(II) acetate, followed by treatment with potassium hydroxide/ sodium borohydride, hydroxylates the double bond and allows for direct cyclization to frontalin.