Synthesis of the marine dibromooxoindoline convolutamydine C

CS Miah, CJ Moody, IC Richards, Alexandra Martha Zoya Slawin

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51 Citations (Scopus)

Abstract

A synthesis of the marine 4,6-dibromo-3-hydroxyoxoindoline convolutamydine C3 is described. The key steps are the rhodium(II) perfluorobutyramide catalysed cyclisation of diazoamide 17 to give the oxoindoline 18, and the subsequent high yielding one-pot hydrolysis-decarboxylation-oxidation of 19 to 20. X-Ray crystal structures have been determined for the diazoamides 10 and 17 and for the oxoindolines 11 and 13.

Original languageEnglish
Pages (from-to)2405-2412
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number16
DOIs
Publication statusPublished - 21 Aug 1997

Keywords

  • CARBOMETHOXY-ALPHA-DIAZOACETANILIDES
  • BRYOZOAN AMATHIA-CONVOLUTA
  • NATURAL-PRODUCTS
  • CHEMOSELECTIVITY
  • SUBSTITUENT
  • CARBENOIDS
  • INSERTION
  • OXIDATION
  • REAGENT

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