0000000000512489
AUTHOR
Tadeusz Librowski
Stereochemistry of terpene derivatives. Part 7: Novel rigidified amino acids from (+)-3-carene designed as chiral GABA analogues
Abstract Several novel cyclopropyl-rigidified γ- and δ-amino acids 3 – 4 have been prepared starting from monoterpene (+)-3-carene 2 . These compounds are proposed as chiral analogues of γ-aminobutyric acid (GABA) 1 and are expected to be of interest as potential inhibitors of GABA receptors.
Stereochemistry of terpene derivatives. Part 3: Hydrolytic kinetic resolution as a convenient approach to chiral aminohydroxyiminocaranes with local anaesthetic activity
Abstract We have developed a stereoselective hydrolytic kinetic resolution process for diastereoisomeric mixtures of epoxyiminocarene intermediates in the presence of ( R , R )-(−)-(salen)Co(III)OAc catalyst, this was applied as the first step in the synthesis of novel chiral aminohydroxyiminocarane derivatives with local anaesthetic activity. The absolute configuration of the product was confirmed by X-ray crystallography.