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

✍ Scribed by Jürgen Schulz; David Gani

Book ID: 104255979
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 256 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(96)02229-0

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✦ Synopsis

A new and efficient route to (-)-(1R,2R,4R,6S)-l,6-epoxy-4-benzyloxycyclohexan-2-ol is described starting from (-)-quinic acid. The pivotal step involves a La3+-induced reversal of the diastet~eoselectivity for the borchydride reduction of an imm'medi~ cyclnhexan-4-one. (IR,2R,4R,6R)-6-Propyloxycyclobexan-1,2,4-triol 1-phosphate, predicted to be a submicromolar inhibitor of inositol m(mot0hospimfase, was pccparcd from tbe epoxide in 20~ yield and displayed the expected imemcy.

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