Evolution of a synthetic strategy: Total synthesis of (±)- welwitindolinone A isonitrile

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

Research output: Contribution to journalArticle

126 Scopus citations

Abstract

An efficient and highly stereoselective total synthesis of the natural product (±)-welwitindolinone A isonitrile (1) is described. The bicyclo[4.2.0]octane core of 1 was established by a regio- and diastereoselective [2+2] ketene cycloaddition. The C12 quaternary center and vicinal stereogenic chlorine were installed in a single operation with excellent stereocontrol via a chloronium ion mediated semipinacol rearrangement. Described strategies for construction of the spiro-oxinole include a Sml 2-LiCl mediated reductive cyclization and a novel anionic cyclization that simultaneously constructs the spiro-oxindole and vinyl isonitrile moieties.

Original languageEnglish (US)
Pages (from-to)2087-2100
Number of pages14
JournalJournal of the American Chemical Society
Volume130
Issue number6
DOIs
StatePublished - Feb 13 2008

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Reisman, S. E., Ready, J. M., Weiss, M. M., Hasuoka, A., Hirata, M., Tamaki, K., Ovaska, T. V., Smith, C. J., & Wood, J. L. (2008). Evolution of a synthetic strategy: Total synthesis of (±)- welwitindolinone A isonitrile. Journal of the American Chemical Society, 130(6), 2087-2100. https://doi.org/10.1021/ja076663z