A mild and efficient synthesis of oxindoles: Progress towards the synthesis of welwitindolinone A isonitrile

Joseph M. Ready, Sarah E. Reisman, Makoto Hirata, Matthew M. Weiss, Kazuhiko Tamaki, Timo V. Ovaska, John L. Wood

Research output: Contribution to journalArticle

70 Scopus citations

Abstract

The complete carbon skeleton of welwitindolinone A isonitrile has been prepared by using a [2+2] cycloaddition to establish the bicyclo[4.2.0]octane core and a Sml2-mediated intramolecular reductive cyclization between an enone and an aryl isocyanate to stereoselectively install the spiro-oxindole (see scheme; DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene).

Original languageEnglish (US)
Pages (from-to)1270-1272
Number of pages3
JournalAngewandte Chemie - International Edition
Volume43
Issue number10
DOIs
StatePublished - Feb 27 2004

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Keywords

  • Alkaloids
  • Natural products
  • Samarium
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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