Kinetic vs. thermodynamic control in intramolecular diene cyclozirconation: Synthesis of elemol

Article abstract of DOI:10.1016/00404-0399(50)1392-U

We predicted (ZINDO) that the major diastereomer from the equilibrating cyclozirconation of the α-terpineol derived diene 1 should be, after oxygenation, the diol 2. We have confirmed this by converting 2 to (+)-elemol 8. The diastereomeric control of the cyclozirconation under kinetic conditions is also striking, providing diol 3.