Journal of the American Chemical Society 2004-04-28

Total synthesis of (+/-)-perophoramidine.

James R Fuchs, Raymond L Funk

Index: J. Am. Chem. Soc. 126 , 5068-5069, (2004)

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Abstract

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.

Related Compounds

  • 6-bromoindole

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