Issue 16, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
27 Dec 2017
Accepted
29 Jan 2018
First published
07 Feb 2018
This article is Open Access
Creative Commons BY license

Chem. Commun., 2018,54, 2008-2011

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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