: A very short stereoselective synthesis of enantiomerically pure (3S, 4aS, 10aR)-quinagolide has been developed. The key steps involved are a copper-catalyzed regioselective arylation of (S)-epichlorohydrin with 1,6-dimethoxynaphthalene and a diastereoselective trans-reduction of a cyclic enamine intermediate. The possibility to use both enantiomers of epichlorohydrin and the diastereodivergency found in the reduction process paves the way for a general preparation also in the nonracemic form of chiral trans-fused 3-substituted octahydrobenzo[g]quinolines that are privileged structures in medicinal chemistry.

Streamlined Stereoselective Entry to (−)-Quinagolide and to 3-Substituted Octahydrobenzo[g]-Quinolines

Lucrezia Margherita Comparini;Lucilla Favero;Sebastiano Di Pietro;Mauro Pineschi
2024-01-01

Abstract

: A very short stereoselective synthesis of enantiomerically pure (3S, 4aS, 10aR)-quinagolide has been developed. The key steps involved are a copper-catalyzed regioselective arylation of (S)-epichlorohydrin with 1,6-dimethoxynaphthalene and a diastereoselective trans-reduction of a cyclic enamine intermediate. The possibility to use both enantiomers of epichlorohydrin and the diastereodivergency found in the reduction process paves the way for a general preparation also in the nonracemic form of chiral trans-fused 3-substituted octahydrobenzo[g]quinolines that are privileged structures in medicinal chemistry.
2024
Sardelli, Francesca; Comparini, LUCREZIA MARGHERITA; Favero, Lucilla; DI PIETRO, Sebastiano; Ryberg, Per; Pineschi, Mauro
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/1223152
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