Synthesis of the acutumine spirocycle via a radical-polar crossover reaction.
A new radical-polar crossover reaction was developed that consists of intramolecular conjugate addition of an aryl radical followed by enolate formation and hydroxylation. A C-C bond, a C-O bond, and two congested stereocenters are created in the process. The product is obtained as a single isomer. The method was used to synthesize the spirocyclic subunit of the alkaloid acutumine.
Li
Fang
F
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, USA.
Castle
Steven L
SL
D000470:Alkaloids / Q000737:chemistry*; D000577:Amides / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry
D000470:Alkaloids; D000577:Amides; D005609:Free Radicals; D007454:Iodides; D013141:Spiro Compounds; D014753:Vinyl Compounds; C442344:acutumine