SYNTHESIS OF (-)-INDOLACTAM-V

  • MASCAL, M
  • MOODY, C J
  • SLAWIN, A M Z
  • WILLIAMS, D J
Publication date
April 1992

Abstract

A stereospecific 7-step synthesis of (-)-indolactam V1 from tryptophan methyl ester is described. The key steps are the photocyclisation of the dichloroamide 6 to give the isomeric 7-hydroxy-7-isopropyl-pyrrolo[4,3,2-fg][3]benzazocines 16 + 18 and the nitrene-mediated ring expansion of the derived azide 5 to give the 9-membered imine 4. The synthesis is completed by stereoselective reduction of the imine bond and N-methylation.</p

Extracted data

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