Journal
CHEMICAL SCIENCE
Volume 4, Issue 3, Pages 1059-1063Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2sc21723f
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Funding
- National Institutes of Health [R01 NS045684]
- Novartis Fellowship
- Lieberman Fellowship
- Stanford Graduate Fellowship
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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.
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