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

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 (...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2004-02, Vol.43 (10), p.1270-1272
Main Authors: Ready, Joseph M., Reisman, Sarah E., Hirata, Makoto, Weiss, Matthew M., Tamaki, Kazuhiko, Ovaska, Timo V., Wood, John L.
Format: Article
Language:English
Subjects:
alkaloids
natural products
samarium
total synthesis
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Summary: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).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200353282