2) via its lithium enolate, but the aldol adduct was produced as a 1:1 mixture of epimeric secondary alcohols that proved difficult to separate. While it is not clear whether the configuration of this hydroxyl group is important, we desired to produce material that was isomerically-pure. To achieve this goal, we utilized Paterson's procedure for stereocontrolled aldol reactions via (-)-Bchlorodiisopinocampheylborane [(-)-DIP-Cl] derived boron enolates. The dimethylacetal protecting group within the products was cleaved in a subsequent hydrolytic step. Thus, coupling 11 with ent-pinonaldehyde (ent-2) delivered aldol dimer 7 in 56% yield as an 8:1 ratio of alcohols over two steps (the configuration of the formed hydroxyl stereocenter was defined based on analogy). By simply using pinonaldehyde (2) in the reaction with 11 we were able to access the diastereomeric aldol dimer 8 in a controlled manner. Both compounds were isolated as highly viscous, honey-like oils at room temperature and ambient pressure.