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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Highly diastereoselective synthesis of enantiopure naphthylaminoalcohols with analgesic properties
Ornella Azzolina1, Simona Collina, Mariangela Urbano
1Dipartimento di Chimica Farmaceutica, Università di Pavia, Viale Taramelli 12, I-27100, Pavia, Italy. ornella.azzolina@unipv.it
Abstract:
The diastereoselective synthesis via Grignard reaction of enantiopure analgesic naphthylaminoalcohols has been performed. The chiral racemic key intermediate 3-dimethylamino-2-methyl-1-(naphthalen-2-yl)propan-1-one and enantiomers were prepared and transformed into the desired compounds by addition of the organometallic reagent. The chemical characterization of all diastereoisomers was accomplished by 1H NMR and HPLC analyses and the absolute configuration assigned by CD spectroscopy. The in vitro and in vivo profile has also been evaluated.
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