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Issue 16, 2018
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Expeditious synthesis of polyacetylenic water hemlock toxins and their effects on the major GABAA receptor isoform

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Abstract

Classical synthetic approaches to highly unsaturated polyene/yne natural products rely on iterative cross-coupling of linear fragments. Herein, we present an expeditious and unified approach to the unsaturated backbone of polyacetylenes via domino cuprate addition/4π-electrocyclic ring opening of a stereodefined cyclobutene intermediate. This sets the stage for a detailed biological assessment of the role of Virol A and Cicutoxin as inhibitors of GABA induced chloride currents, providing further insight into the interaction of these highly potent toxins towards the GABAA receptor, including the structure–activity relationship of the derivatives.

Graphical abstract: Expeditious synthesis of polyacetylenic water hemlock toxins and their effects on the major GABAA receptor isoform

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Publication details

The article was received on 27 Dec 2017, accepted on 29 Jan 2018 and first published on 07 Feb 2018


Article type: Communication
DOI: 10.1039/C7CC09801D
Citation: Chem. Commun., 2018,54, 2008-2011
  • Open access: Creative Commons BY license
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    Expeditious synthesis of polyacetylenic water hemlock toxins and their effects on the major GABAA receptor isoform

    M. Berger, Y. Chen, K. Bampali, M. Ernst and N. Maulide, Chem. Commun., 2018, 54, 2008
    DOI: 10.1039/C7CC09801D

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