C3‐Symmetric Tricyclo[2.2.1.02,6]heptane‐3,5,7‐triol |
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Abstract: | A straightforward access to a hitherto unknown C 3‐symmetric tricyclic triol both in racemic and enantiopure forms has been developed. Treatment of 7‐tert ‐butoxynorbornadiene with peroxycarboxylic acids provided mixtures of C 1‐ and C 3‐symmetric 3,5,7‐triacyloxynortricyclenes via transannular π‐cyclization and replacement of the tert ‐butoxy group. By refluxing in formic acid, the C 1‐symmetric esters were converted to the C 3‐symmetric formate. Hydrolysis gave diastereoisomeric triols, which were separated by recrystallization. Enantiomer resolution via diastereoisomeric tri(O ‐methylmandelates) delivered the target triols on a gram scale. The pure enantiomers are useful as core units of dopants for liquid crystals. |
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Keywords: | C3 symmetry chiral resolution neighboring-group effects nortricyclene transannular cyclization |
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