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

Add time:07/28/2019    Source:sciencedirect.com

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 cycloxan-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.

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