(1R,2R,3S,5R)-(-)-2,3-Pinanediol is a bicyclic monoterpene diols that has been shown to induce differentiation of S91 melanoma and PC12 pheochromocytoma cells and thus provide possible therapeutic and sunless tanning use. (1R,2R,3S,5R)-(-)-2,3-Pinanediol is a microbial oxidation product of (-)-β-pinene, a flavor and fragrance monoterpene.
Under nitrogen protection, (-)-α-pinene (15 mL, 97 mmol) was dissolved in 100 mL of tert-butanol with Me3NO-2H2O (11 g, 102 mmol). Pyridine (7 mL) and osmium tetroxide (51 mg, 0.2 mmol) were added sequentially and heated to reflux. After 20 hours of reaction, the completion of the reaction was confirmed by TLC monitoring. The reaction mixture was cooled to room temperature, NaHSO3 (1.2 g, 12 mmol) was added and stirred for 1 hour. The reaction solution was transferred to a partition funnel and the organic phase was separated. The aqueous phase was extracted with ether (3 x 20 mL), the organic phases were combined and dried with anhydrous sodium sulfate. After filtration, the solvent was removed by rotary evaporator. The product was purified by column chromatography (petroleum ether:ethyl acetate=30:1) to give 14 g of white solid in 85% yield.
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