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

Ready Joseph M. | Zendy; Reisman Sarah E. | Zendy; Hirata Makoto | Zendy; Weiss Matthew M. | Zendy; Tamaki Kazuhiko | Zendy; Ovaska Timo V. | Zendy; Wood John L. | Zendy

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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).

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