A mild and efficient synthesis of oxindoles: Progress towards the synthesis of welwitindolinone A isonitrile

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

doi:10.1002/anie.200353282

A mild and efficient synthesis of oxindoles: Progress towards the synthesis of welwitindolinone A isonitrile

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

Research output: Contribution to journal › Article › peer-review

79 Scopus citations

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 Sml₂-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).

Original language	English (US)
Pages (from-to)	1270-1272
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	43
Issue number	10
DOIs	https://doi.org/10.1002/anie.200353282
State	Published - Feb 27 2004

Keywords

Alkaloids
Natural products
Samarium
Total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200353282

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title = "A mild and efficient synthesis of oxindoles: Progress towards the synthesis of welwitindolinone A isonitrile",

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 Sml2-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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T1 - A mild and efficient synthesis of oxindoles

T2 - Progress towards the synthesis of welwitindolinone A isonitrile

AU - Ready, Joseph M.

AU - Reisman, Sarah E.

AU - Hirata, Makoto

AU - Weiss, Matthew M.

AU - Tamaki, Kazuhiko

AU - Ovaska, Timo V.

AU - Wood, John L.

PY - 2004/2/27

Y1 - 2004/2/27

N2 - 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 Sml2-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).

AB - 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 Sml2-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).

KW - Alkaloids

KW - Natural products

KW - Samarium

KW - Total synthesis

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A mild and efficient synthesis of oxindoles: Progress towards the synthesis of welwitindolinone A isonitrile

Abstract

Keywords

ASJC Scopus subject areas

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