(-)-Isopinocampheol could be made from the below reactional routes.

A 300-ml., three-necked flask, equipped with a magnetic stirring bar, thermometer, pressure-equalizing dropping funnel fitted with septum inlet adapter, and reflux condenser fitted with a hose adapter leading to a mineral oil bubbler, is charged with 10.0 ml. (0.100 mole) of borane–methyl sulfide complex and 30 ml. of tetrahydrofuran. The flask is immersed in an ice-water bath as 27.2 g. (31.7 ml., 0.200 mole) of (+)-α-pinene is added dropwise at 0–3° to the well-stirred reaction mixture over a period of 15 minutes. The (-)-diisopinocampheylborane [(-)-di-3-pinanylborane] precipitates as a white solid as the reaction proceeds. Following addition, the reaction mixture is stirred for 3.5 hours at 0°. Under a slow stream of nitrogen, the outlet hose adapter on the reflux condenser is connected with rubber vacuum hose to a vacuum trap which is then cooled in an acetone–dry ice bath. The dimethyl sulfide and tetrahydrofuran are bulb-to-bulb vacuum-distilled (0.1 mm.) with the reaction flask in a room temperature water bath. When only a dry, white solid residue remains, the vacuum is released with nitrogen. The flask is again placed under a slight positive pressure of nitrogen. The solid is slurried in 36 ml. of tetrahydrofuran at room temperature. An additional 4.08 g. (4.76 ml., 0.030 mole) of (+)-α-pinene is added. The resulting slurry is stirred at room temperature for 5 minutes and then stored under nitrogen in a closed system in a cold room at 4° for 3 days. The flask is then removed from the cold room and immersed in an ice-water bath. Under a slow stream of nitrogen, the outlet adapter on the reflux condenser is again connected to the mineral oil bubbler. The excess hydride is destroyed by the slow, dropwise addition of 8 ml. of methanol, followed by the addition in one portion of 36.6 ml. of 3 M aqueous sodium hydroxide. The borinic acid intermediate is now oxidized by the dropwise addition of 24 ml. of 30% aqueous hydrogen peroxide to the well-stirred reaction mixture at 35° ± 3°. After the hydrogen peroxide addition is complete, the ice-water bath is replaced with a warm-water bath and the reaction mixture is stirred for one hour at 50–55° and then cooled to room temperature. The aqueous layer is saturated with sodium chloride and 50 ml. of diethyl ether is added. The upper organic layer is removed, and the aqueous layer is extracted with two 100-ml. portions of ether. The organic layer and extracts are combined, dried over anhydrous potassium carbonate, filtered, and concentrated to an oil on a rotary evaporator at 60° (15 mm.). The crude product is fractionally distilled using a 30-cm. column packed with glass helices, giving 24.7 g. (80%) of (-)-isopinocampheol, b.p. 60–65° (0.1 mm.). The distillate crystallizes completely in the receiver, m.p. 49–55°, 97.5% purity by GC, [α]_D¹⁹ -34.3° (C, 20 in ethanol). Slurrying 4.7 g. in 2.3 ml. of pentane at room temperature, cooling to -78°, collecting on a filter, and air drying gives 3.8 g. of crystalline (-)-isopinocampheol, m.p. 52–55°, purity 99.2% by GC, [α]_D¹⁹ -34.9° (C, 20 in ethanol).