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

Autor:	Comparini LM; Department of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, Italy. Mauro.pineschi@unipi.it., Menichetti A; Department of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, Italy. Mauro.pineschi@unipi.it., Favero L; Department of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, Italy. Mauro.pineschi@unipi.it., Di Pietro S; Department of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, Italy. Mauro.pineschi@unipi.it., Badalassi F; Chemical Development, Global Pharmaceutical R&D, Ferring Pharmaceuticals A/S, Amager Strandvej 405, DK 2770 Kastrup, Denmark. Per.Ryberg@ferring.com., Ryberg P; Chemical Development, Global Pharmaceutical R&D, Ferring Pharmaceuticals A/S, Amager Strandvej 405, DK 2770 Kastrup, Denmark. Per.Ryberg@ferring.com., Pineschi M; Department of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, Italy. Mauro.pineschi@unipi.it.
Jazyk:	angličtina
Zdroj:	Organic & biomolecular chemistry [Org Biomol Chem] 2023 Aug 09; Vol. 21 (31), pp. 6389-6396. Date of Electronic Publication: 2023 Aug 09.
DOI:	10.1039/d3ob00946g
Abstrakt:	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 (3 S ,4a S ,10a R )-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.
Databáze:	MEDLINE
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