The stereoselective reduction of a diastereoisomeric mixture of benzo[g]octahydroquinolinium ion was examined in detail. A diastereoselective borohydride reduction in combination with an efficient deacylative enzymatic resolution of its & beta;-aminoester precursor are the key steps for a stereoselective installation of the three chiral centres present in the (3S,4aS,10aR)-eutomer of the medicinal drug quinagolide. The obtained data paves the way for an easy and practical attainment of chiral 3-substituted octahydrobenzo[g]quinolines that are privileged structures in medicinal chemistry.

Development of an asymmetric formal synthesis of (-)-quinagolide via enzymatic resolution and stereoselective iminium ion reduction

Comparini, Lucrezia Margherita;Favero, Lucilla;Di Pietro, Sebastiano;Pineschi, Mauro
2023-01-01

Abstract

The stereoselective reduction of a diastereoisomeric mixture of benzo[g]octahydroquinolinium ion was examined in detail. A diastereoselective borohydride reduction in combination with an efficient deacylative enzymatic resolution of its & beta;-aminoester precursor are the key steps for a stereoselective installation of the three chiral centres present in the (3S,4aS,10aR)-eutomer of the medicinal drug quinagolide. The obtained data paves the way for an easy and practical attainment of chiral 3-substituted octahydrobenzo[g]quinolines that are privileged structures in medicinal chemistry.
2023
Comparini, Lucrezia Margherita; Menichetti, Andrea; Favero, Lucilla; Di Pietro, Sebastiano; Badalassi, Fabrizio; Ryberg, Per; Pineschi, Mauro
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/1200187
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