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. 2004 Apr 28;126(16):5068-9.
doi: 10.1021/ja049569g.

Total synthesis of (+/-)-perophoramidine

James R Fuchs  1 , Raymond L Funk
Affiliations

Total synthesis of (+/-)-perophoramidine

James R Fuchs et al. J Am Chem Soc. .

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.

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