doiSerbia

Synthesis of tetrahydrokhusitone: Annulation of the cyclohexane ring by free radical and carbanionic sequence of reactions

Petrović Goran (Faculty of Chemistry, University of Belgrade + Center for Chemistry, Institute for Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro)
Čeković Živorad (Faculty of Chemistry, University of Belgrade, Studentski trg 16, P. O. Box 158 and Center for Chemistry, Institute for Chemistry, Technology and Metallurgy, Njegoševa 12, 11000 Belgrade, Serbia and Montenegro)

The synthesis of norcadinane sesquiterpene tetrahydrokhusitone 1 has been achieved by a new method for annulation of cyclohexane ring involving a sequence of free radical δ-alkylation of the non-activated carbon atom and intramolecular carbanionic alkylation. (–)-Menthol was used as the starting compound.

Keywords: khusitone, norcadinanes, annulation of the cyclohexane ring, 1,5-hydrogen transfer, cycloalkylation, isomerization, tetrahydrokhusitone.