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Issue 3, 2013
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Modular synthesis of the pentacyclic core of batrachotoxin and select batrachotoxin analogue designs

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Abstract

Pentacyclic analogues of the potent voltage-gated sodium ion channel agonist batrachotoxin can be accessed through an intermediate furan by exploiting Diels–Alder cycloaddition reactions with ring-strained dienophiles. The use of 3-bromofuran as a 1,2-dianion equivalent, the application of carbamate reductive N-alkylation for homomorpholine ring assembly, and the demonstration of CsF as an effective reagent for generating benzyne, cyclohexyne, and related dienophiles underscore this work.

Graphical abstract: Modular synthesis of the pentacyclic core of batrachotoxin and select batrachotoxin analogue designs

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Publication details

The article was received on 11 Oct 2012, accepted on 09 Nov 2012 and first published on 21 Dec 2012


Article type: Edge Article
DOI: 10.1039/C2SC21723F
Citation: Chem. Sci., 2013,4, 1059-1063
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    Modular synthesis of the pentacyclic core of batrachotoxin and select batrachotoxin analogue designs

    A. Sloan Devlin and J. Du Bois, Chem. Sci., 2013, 4, 1059
    DOI: 10.1039/C2SC21723F

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