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