SYNTHESIS OF (-)-INDOLACTAM-V

M MASCAL, C J MOODY, A M Z SLAWIN, D J WILLIAMS

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47 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)823-830
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number7
Publication statusPublished - 7 Apr 1992

Keywords

  • TUMOR PROMOTERS TELEOCIDINS
  • BIOSYNTHESIS
  • REQUIREMENTS
  • LYNGBYATOXIN
  • MODULATORS

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