Dihydromyrcenol is used as a hydrated masked form of citronellene
in olefin cross-metathesis reactions in order to solve the selectivity
problem that results from the presence of two double bonds in many
terpenes. Several ruthenium catalysts are evaluated, with the best,
M71-SIPr, utilized in the cross-metathesis of dihydromyrcenol with
various olefins affording the expected products in good yields.
It is shown that the masked double bond can be regenerated via an
acid-catalyzed elimination reaction and the product is then subjected
to a further cross-metathesis reaction with a second olefin.
terpenoids - olefin metathesis - chemoselectivity - agro-resources - dihydromyrcenol
