The mechanism of the thermal rearrangement of the marasmane sesquiterpene (+)-isovelleral. Cyclopropane ring closure via an intramolecular ene reaction
Abstract
The reversible thermal conversion of the fungal sesquiterpene Isovelleral (2) into (1) is a unique Intramolecular ene reaction proceeding via the bicyclic enol (3), which is demonstrated by kinetic studies, deuterium incorporation, and the trapping of (3).