A Mild and Efficient Synthesis of Oxindoles: Progress Towards the Synthesis of Welwitindolinone A Isonitrile

Authors

  • Joseph M. Ready Dr.,

    1. Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
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  • Sarah E. Reisman,

    1. Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
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  • Makoto Hirata Dr.,

    1. Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
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  • Matthew M. Weiss Dr.,

    1. Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
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  • Kazuhiko Tamaki Dr.,

    1. Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
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  • Timo V. Ovaska Dr.,

    1. Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
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  • John L. Wood Prof. Dr.

    1. Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
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  • We gratefully acknowledge financial support from Yamanouchi, Merck, Pfizer, and Amgen. J.M.R. is the recipient of an NIH postdoctoral fellowship. K.R. thanks Sankyo Co., LTD.; M.H. thanks Daiso Co., LTD., M.M.W. thanks Bristol Myers Squibb for a graduate fellowship.

Abstract

original image

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 SmI2-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).

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