SYNTHESIS OF 1R,2R,4R,6S)-1,6-EPOXY-4-BENZYLOXYCYCLOHEXAN-2-OL, A KEYPRECURSOR TO INOSITOL MONOPHOSPHATASE INHIBITORS, FROM (-)-QUINIC ACID

A new and efficient route to 1R,2R,4R,6S)-1,6-epoxy-4-benzyloxycyclohe xane-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,6 R)-6-Propyloxycyclohexan-1,2,4-triol l-phosphate, predicted to be a su bmicromolar inhibitor of inositol monophosphatase, was prepared from t he epoxide in 20% yield and displayed the expected potency. Copyright (C) 1996 Elsevier Science Ltd