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Synthesis of the Core Structure of Acutumine

2005; American Chemical Society; Volume: 7; Issue: 6 Linguagem: Inglês

10.1021/ol050020b

1523-7060

Matthew D. Reeder, Gourishetty Srikanth, Spencer B. Jones, Steven L. Castle,

Traditional and Medicinal Uses of Annonaceae

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.