Synthesis of (-)-(1R,2R,4R,6S)-1,6-epoxy-4-benzyloxycyclohexan-2-ol, a key precursor to inositol monophosphatase inhibitors, from (-)-quinic acid

Article abstract of DOI:10.1016/S0040-4039(96)02229-0

A new and efficient route to (-)-(1R,2R,4R,6S)-1,6-epoxy-4-benzyloxycyclohexan-2-ol is described starting from (-)-quinic acid. The pivotal step involves a La³⁺-induced reversal of the diastereoselectivity for the borohydride reduction of an intermediate cyclohexan-4-one. (1R,2R,4R,6R)-6-Propyloxycyclohexan-1,2,4-triol 1-phosphate, predicted to be a submicromolar inhibitor of inositol monophosphatase, was prepared from the epoxide in 20% yield and displayed the expected potency.