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

Ready, Joseph M. and Reisman, Sarah E. and Hirata, Makoto and Weiss, Matthew M. and Tamaki, Kazuhiko and Ovaska, Timo V. and Wood, John L. (2004) A Mild and Efficient Synthesis of Oxindoles: Progress Towards the Synthesis of Welwitindolinone A Isonitrile. Angewandte Chemie International Edition, 43 (10). pp. 1270-1272. ISSN 1433-7851. https://resolver.caltech.edu/CaltechAUTHORS:20170404-071621138

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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).


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.200353282DOIArticle
http://onlinelibrary.wiley.com/wol1/doi/10.1002/anie.200353282/abstractPublisherArticle
http://onlinelibrary.wiley.com/wol1/doi/10.1002/anie.200353282/suppinfoRelated ItemSupporting Information
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2004 WILEY-VCH Verlag GmbH & Co. Issue online: 25 Feb 2004. Version of Record online: 11 Feb 2004. Manuscript Received: 10 Nov 2003. We 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.
Funders:
Funding AgencyGrant Number
YamanouchiUNSPECIFIED
MerckUNSPECIFIED
PfizerUNSPECIFIED
AmgenUNSPECIFIED
Bristol-Myers SquibbUNSPECIFIED
NIH Postdoctoral FellowshipUNSPECIFIED
Sankyo Co., Ltd.UNSPECIFIED
Daiso Co., Ltd.UNSPECIFIED
Subject Keywords:alkaloids · natural products · samarium · total synthesis
Issue or Number:10
Record Number:CaltechAUTHORS:20170404-071621138
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170404-071621138
Official Citation:Ready, J. M., Reisman, S. E., Hirata, M., Weiss, M. M., Tamaki, K., Ovaska, T. V. and Wood, J. L. (2004), A Mild and Efficient Synthesis of Oxindoles: Progress Towards the Synthesis of Welwitindolinone A Isonitrile. Angew. Chem. Int. Ed., 43: 1270–1272. doi: 10.1002/anie.200353282
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:75662
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:04 Apr 2017 15:06
Last Modified:03 Oct 2019 16:52

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