4.5 Article

Asymmetric Total Synthesis of All Rugulovasine Stereoisomers and Preliminary Evaluation of Their Biological Properties

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2022, Issue 17, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200315

Keywords

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Funding

  1. Italian Ministry for University and Research (MUR) [2020AEX4TA]
  2. University of Urbino
  3. Universita degli Studi di Urbino Carlo Bo within the CRUI-CARE Agreement

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A unified enantioselective synthesis and biological evaluation of all rugulovasine stereoisomers were reported. A divergent approach was used to synthesize the unsaturated oxaspirolactone moiety, allowing rapid synthesis of all stereoisomers. These compounds showed preferred selectivity for the serotonin 1 A receptor.
A unified enantioselective synthesis and the biological evaluation of all rugulovasine stereoisomers are reported. The syntheses are centered on the divergent and stereochemical modular combination of each enantiomer of 4-amino Uhle's ketone and a methacrylate derivative to build the unsaturated oxaspirolactone moiety by the Dreiding-Schmidt reaction, followed by Fukuyama alkylation to afford the required N-methyl secondary amine in excellent yield. The modularity of this divergent approach, the diastereoselectivities of the reactions, and the late-stage site-selective methylation permit the rapid asymmetric syntheses of all rugulovasine stereoisomers, including the first total syntheses of optically pure (+)- and (-)-rugulovasine B and their trideuteromethylated derivatives. All enantiopure stereoisomers of rugulovasine were tested for their binding affinities to dopamine, serotonin, and adrenergic neuroreceptors, revealing their preferred selectivity for the serotonin 1 A receptor.

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