Intramolecular Alkylation Route to the Bicyclononane Ring System. A Total Synthesis of dl-Clovene

Article abstract of DOI:10.1021/jo00162a004

A formal total synthesis of dl-clovene (9) is described.The synthesis is highlighted by the efficient intramolecular alkylation of trisubstituted cyclohexenone 11b to give 5-(2-ethylallyl)-1-methylbicyclo<3.3.1>non-2-en-4-one (13b) in 80percent isolated yield.The preparation of 11b follows an alkylation route starting with the enol ether 3 of cyclohexane-1,3-dione.