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A Mild and Efficient Synthesis of Oxindoles: Progress Towards the Synthesis of Welwitindolinone A Isonitrile
Author(s) -
Ready Joseph M.,
Reisman Sarah E.,
Hirata Makoto,
Weiss Matthew M.,
Tamaki Kazuhiko,
Ovaska Timo V.,
Wood John L.
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200353282
Subject(s) - oxindole , chemistry , intramolecular force , cycloaddition , bicyclic molecule , octane , isocyanate , enone , aryl , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , alkyl , polyurethane
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 SmI 2 ‐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).