4 years ago

C3-Symmetric Tricyclo[,6]heptane-3,5,7-triol

Günter Haufe, Peer Kirsch, Constantin-Gabriel Daniliuc, Volodymyr Kozel
A straightforward access to a hitherto unknown C3-symmetric tricyclic triol both in racemic and enantiopure forms has been elaborated. Treatment of 7-tert-butoxynorbornadiene with peroxycarboxylic acids provided mixtures of C1- and C3-symmetric 3,5,7-triacyloxy-nortricyclenes via transannular π-cyclization and substitution of the tert-butoxy group. Refluxing in formic acid, the C1-symmetric esters were converted to the C3-symmetric formate. Hydrolysis gave diastereoisomeric triols, which were separated by recrystallization. Enantiomer resolution via diastereoisomeric tri(O-methylmandelates) delivered the target triols in gram scale. The pure enantiomers are useful as core units of dopants for liquid crystals.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201709279

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