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Synthesis of antimitotic analogs of the microtubule stabilizing sponge alkaloid ceratamine A

TitleSynthesis of antimitotic analogs of the microtubule stabilizing sponge alkaloid ceratamine A
Publication TypeJournal Article
Year of Publication2008
AuthorsNodwell, M, Riffell, JL, Roberge, M, Andersen, RJ
JournalOrganic Letters
Volume10
Pagination1051-1054
Date PublishedMar
ISBN Number1523-7060
Abstract

Antimitotic analogs of the microtubule stabilizing sponge alkaloid ceratamine A (1) have been synthesized starting from tribromoimidazole. A key step in the synthesis is the formation of the azepine ring via an intramolecular Buchwald coupling between a vinyl bromide and a N-methyl amide. This represents the first synthesis of a fully unsaturated imidazo[4,5,d]azepine. NMR data obtained for the synthetic ceratamine analogs has provided support for the structure assigned to the natural product.

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