Total synthesis of (+/-)-perophoramidine.
The first total synthesis of racemic perophoramidine is described. The key step features the highly stereoselective introduction of the vicinial quaternary centers via base-promoted carbon-carbon bond formation between a 3-alkylindole and a 3-bromo-3-alkylindolin-2-one. This transformation presumably proceeds through a conjugate addition or Diels-Alder cycloaddition of the 3-alkylindole with a 3-alkylindol-2-one intermediate.
Fuchs
James R
JR
Department of Chemistry, Pennsylvania State University, 16802 USA.
Funk
Raymond L
RL
D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D006576:Heterocyclic Compounds, 4 or More Rings; D006846:Hydrocarbons, Halogenated; D007783:Lactones; C483283:communesin B; C472225:perophoramidine