A Mild and Efficient Synthesis of Oxindoles: Progress Towards the Synthesis of Welwitindolinone A Isonitrile†
Joseph M. Ready Dr.
Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
Search for more papers by this authorSarah E. Reisman
Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
Search for more papers by this authorMakoto Hirata Dr.
Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
Search for more papers by this authorMatthew M. Weiss Dr.
Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
Search for more papers by this authorKazuhiko Tamaki Dr.
Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
Search for more papers by this authorTimo V. Ovaska Dr.
Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
Search for more papers by this authorJohn L. Wood Prof. Dr.
Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
Search for more papers by this authorJoseph M. Ready Dr.
Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
Search for more papers by this authorSarah E. Reisman
Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
Search for more papers by this authorMakoto Hirata Dr.
Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
Search for more papers by this authorMatthew M. Weiss Dr.
Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
Search for more papers by this authorKazuhiko Tamaki Dr.
Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
Search for more papers by this authorTimo V. Ovaska Dr.
Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
Search for more papers by this authorJohn L. Wood Prof. Dr.
Department of Chemistry, Yale University, Sterling Chemistry Laboratory, PO Box 208107, New Haven, CT 06520–8107, USA, Fax: (+1) 203-432-6144
Search for more papers by this authorWe 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.
Graphical 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 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).
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z53282_s.pdf or from the author.
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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