Synthesis of (-)-indolactam V

Mark Mascal, Christopher J. Moody, Alexandra M Z Slawin, David J. Williams

Research output: Contribution to journalArticle

45 Scopus citations

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-isopropylpyrrolo[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 (US)
Pages (from-to)823-830
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number7
StatePublished - 1992
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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