Expeditious synthesis of polyacetylenic water hemlock toxins and their effects on the major GABA receptor isoform

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...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018-02, Vol.54 (16), p.28-211
Main Authors: Berger, Martin, Chen, Yong, Bampali, Konstantina, Ernst, Margot, Maulide, Nuno
Format: Article
Language:English
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Summary: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 GABA A receptor, including the structure-activity relationship of the derivatives. Classical synthetic approaches to highly unsaturated polyene/yne natural products rely on iterative cross-coupling of linear fragments.
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc09801d