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C 3 ‐Symmetric Tricyclo[2.2.1.0 2,6 ]heptane‐3,5,7‐triol
Author(s) -
Kozel Volodymyr,
Daniliuc ConstantinGabriel,
Kirsch Peer,
Haufe Günter
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201709279
Subject(s) - enantiopure drug , formate , chemistry , triol , enantiomer , heptane , formic acid , hydrolysis , recrystallization (geology) , stereochemistry , medicinal chemistry , organic chemistry , diol , enantioselective synthesis , catalysis , paleontology , biology
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.