A novel skeletal rearrangement of bicyclo(2.2.2)octenes through bicyclo(3.2.1)octene system: synthesis of (±)-hinesol and (±)-10--hinesol

Acid catalysed rearrangement of the endo-alcohol (9) leads to the ketones (11) and (12) having the bicyclo(3.2.1) and bicyclo(2.2.2) moieties. An efficient entry into spiro(4.5)decane and eremane system, as exemplified by the total synthesis of (±)-hinesol (2) and its 10-epimer (3) is reported.