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Published on: October 2, 2018
Synthesis of the core structure of acutumine
Matthew D Reeder1, G S C Srikanth, Spencer B Jones
1Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, USA.
Abstract:
[reaction: see text] 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.
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