Stereoselective Synthesis and Isolation of (±)-trans,trans-Cyclohexane-1,2,4,5-tetraol

Abstract

Cyclohexanetetrols belong to the family of cyclitols, a class of natural products known for their diverse bioactivity. Their synthesis has been reported using hydrogen peroxide as a green oxidant and water or tert-butanol as a solvent. Due to the high polarity of those compounds, a green approach for their isolation from aqueous solutions can be challenging. Here, we report the stereoselective synthesis of (±)-trans,trans-cyclohexane-1,2,4,5-tetraol combined with a novel isolation method, where is possible the isolation of the product in excellent yield without the need for derivatization, column chromatography or organic solvent extraction.