Search results for "carane"
showing 2 items of 2 documents
Comparative investigations of hydroxyamine carane derivative and its R,S-diastereoisomers with strong local anesthetic activity
2001
Our previously conducted pharmacological screening led as to the discovery of the strong local anesthetic activity of the compound designated as KP-23. Earlier crystallographic studies revealed that the compound KP-23 crystallized in diastereoisomeric form in lowest symmetry. The aim of these comparative investigations was to evaluate anesthetic activity of KP-23 and its R,S-diastereoisomers, which were synthesized at the Institute of Organic Chemistry, Biochemistry and Biotechnology, Wroclaw University of Technology.
Stereoselective synthesis of carane-based chiral β- and γ-amino acid derivatives via conjugate addition
2015
Abstract Michael addition of dibenzylamine to (−)-tert-butyl isochaminate, prepared in three steps from (−)-perillaldehyde, furnished a carane-based β-amino acid derivative in a highly stereospecific reaction. The resulting amino ester was transformed to the bicyclic amino acid, a promising building block for the synthesis of 1,3-heterocycles and peptidomimetics. The conjugate addition of nitromethane to α,β-unsaturated methyl ester likewise resulted in nitro esters in stereospecific reactions. Catalytic reduction of the nitro group yielded a γ-amino ester. Under acidic conditions, the hydrolysis of the methyl ester resulted in an unexpected aminolactone-type product through rearrangement o…