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Total Synthesis of (±)-Welwitindolinone A Isonitrile

Reisman, Sarah E. and Ready, Joseph M. and Hasuoka, Atsushi and Smith, Catherine J. and Wood, John L. (2006) Total Synthesis of (±)-Welwitindolinone A Isonitrile. Journal of the American Chemical Society, 128 (5). pp. 1448-1449. ISSN 0002-7863. doi:10.1021/ja057640s. https://resolver.caltech.edu/CaltechAUTHORS:20170331-145008719

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Abstract

A highly stereoselective total synthesis of the alkaloid natural product welwitindolinone A isonitrile has been completed. The synthesis utilizes a chloronium ion mediated semi-pinacol rearrangement to simultaneously install the C10 quaternary center and neopentyl chlorine and a novel anionic cyclization to construct the spiro-oxindole with complete stereocontrol.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja057640sDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja057640sPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja057640sPublisherSupporting Information
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2006 American Chemical Society. Received November 9, 2005; Publication Date (Web): January 11, 2006. Financial support was provided by Bristol-Myers Squibb, Yamanouchi, Merck, Amgen, Pfizer, and the NIH (Grant No. 1 R01 CA/GM 93591-01A). S.E.R. thanks Bristol-Myers Squibb for a graduate student fellowship. J.M.R. was the recipient of a NIH postdoctoral fellowship. In addition, we acknowledge and thank C.D. Incarvito for X-ray crystallographic analysis.
Funders:
Funding AgencyGrant Number
Bristol-Myers SquibbUNSPECIFIED
YamanouchiUNSPECIFIED
MerckUNSPECIFIED
AmgenUNSPECIFIED
PfizerUNSPECIFIED
NIH1 R01 CA/GM 93591-01A
NIH Postdoctoral FellowshipUNSPECIFIED
Issue or Number:5
DOI:10.1021/ja057640s
Record Number:CaltechAUTHORS:20170331-145008719
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170331-145008719
Official Citation:Total Synthesis of (±)-Welwitindolinone A Isonitrile Sarah E. Reisman, Joseph M. Ready, Atsushi Hasuoka, Catherine J. Smith, and John L. Wood Journal of the American Chemical Society 2006 128 (5), 1448-1449 DOI: 10.1021/ja057640s
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:75605
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:03 Apr 2017 16:54
Last Modified:15 Nov 2021 16:35

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