title: Synthesis of the core structure of acutumine.
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.
authors.affiliation: Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, USA.
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Reeder
authors.forename: G S C
authors.initials: GS
authors.lastname: Srikanth
authors.forename: Spencer B
authors.initials: SB
authors.lastname: Jones
authors.forename: Steven L
authors.initials: SL
authors.lastname: Castle
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D013141:Spiro Compounds; C442344:acutumine