Integrated synthesis of conduritols A–F using a single chiral building block

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Masatoshi Honzumi, Kou Hiroya, Takahiko Taniguchi and Kunio Ogasawara


Abstract

Six possible diastereomers of conduritols have been synthesized diastereoselectively in an integrated manner starting from a single chiral precursor, which served as a synthetic equivalent of chiral cis-1,4-dihydroxycyclohexa-2,5-diene.


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