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

120 Citations (Scopus)

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

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Cyclization
Cycloaddition
Chlorine
Cycloaddition Reaction
Biological Products
Ions
welwitindolinone A isonitrile
octane
oxindole
semipinacol
ketene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Evolution of a synthetic strategy : Total synthesis of (±)- welwitindolinone A isonitrile. / Reisman, Sarah E.; Ready, Joseph M.; Weiss, Matthew M.; Hasuoka, Atsushi; Hirata, Makoto; Tamaki, Kazuhiko; Ovaska, Timo V.; Smith, Catherine J.; Wood, John L.

In: Journal of the American Chemical Society, Vol. 130, No. 6, 13.02.2008, p. 2087-2100.

Research output: Contribution to journalArticle

Reisman, SE, Ready, JM, Weiss, MM, Hasuoka, A, Hirata, M, Tamaki, K, Ovaska, TV, Smith, CJ & Wood, JL 2008, 'Evolution of a synthetic strategy: Total synthesis of (±)- welwitindolinone A isonitrile', Journal of the American Chemical Society, vol. 130, no. 6, pp. 2087-2100. https://doi.org/10.1021/ja076663z
Reisman, Sarah E. ; Ready, Joseph M. ; Weiss, Matthew M. ; Hasuoka, Atsushi ; Hirata, Makoto ; Tamaki, Kazuhiko ; Ovaska, Timo V. ; Smith, Catherine J. ; Wood, John L. / Evolution of a synthetic strategy : Total synthesis of (±)- welwitindolinone A isonitrile. In: Journal of the American Chemical Society. 2008 ; Vol. 130, No. 6. pp. 2087-2100.
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