Issue 3, 2013

Modular synthesis of the pentacyclic core of batrachotoxin and select batrachotoxin analogue designs

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

Supplementary files

Article information

Article type
Edge Article
Submitted
11 Oct 2012
Accepted
09 Nov 2012
First published
21 Dec 2012

Chem. Sci., 2013,4, 1059-1063

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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