Issue 31, 2023

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

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 β-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.

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

Supplementary files

Article information

Article type
Paper
Submitted
15 Jun 2023
Accepted
18 Jul 2023
First published
24 Jul 2023

Org. Biomol. Chem., 2023,21, 6389-6396

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

L. M. Comparini, A. Menichetti, L. Favero, S. Di Pietro, F. Badalassi, P. Ryberg and M. Pineschi, Org. Biomol. Chem., 2023, 21, 6389 DOI: 10.1039/D3OB00946G

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