American Chemical Society
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Synthesis of the Core Structure of Acutumine

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journal contribution
posted on 2005-03-17, 00:00 authored by Matthew D. Reeder, G. S. C. Srikanth, Spencer B. Jones, Steven L. Castle
The tricyclic core of the bioactive natural product acutumine has been synthesized. Key steps include an oxidative phenolic coupling to form a masked o-benzoquinone, an anionic oxy-Cope rearrangement to construct an all-carbon quaternary center, and a Michael-type cyclization to form an amine-bearing quaternary carbon. The target compound exists in solution as an enol, in contrast to related compounds that are ketones. A model explaining these observations is presented.