Studies directed toward total synthesis of olivin (4), the aglycon of the olivomycin antitumor antibiotics, are described. The key aldehyde 23, containing the tricyclic nucleus of olivin, has been prepared in 14 steps from 3, 5-dimethoxybenzyl chloride. Methods for construction of the olivin hydroxy ketone side chain were also investigated. Attempted addition of trianion 24 to simple aldehydes was unsuccessful. Cyclohexanecarboxaldehyde, a model for ...