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Welwitindolinone C synthetic studies. Construction of the welwitindolinone carbon skeleton via a transannular nitrone cycloaddition

Freeman, David B. and Holubec, Alexandra A. and Weiss, Matthew W. and Dixon, Julia A. and Kakefuda, Akio and Ohtsuka, Masami and Inoue, Munenori and Vaswani, Rishi G. and Ohki, Hidenori and Doan, Brian D. and Reisman, Sarah E. and Stoltz, Brian M. and Day, Joshua J. and Tao, Ran N. and Dieterich, Noah A. and Wood, John L. (2010) Welwitindolinone C synthetic studies. Construction of the welwitindolinone carbon skeleton via a transannular nitrone cycloaddition. Tetrahedron, 66 (33). pp. 6647-6655. ISSN 0040-4020. PMCID PMC2924776. https://resolver.caltech.edu/CaltechAUTHORS:20141217-164835707

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Abstract

Described is the construction of the N-methylwelwitindolinone C core via an efficient strategy that employs a sequential rhodium carbenoid-mediated O–H insertion, Claisen rearrangement and transannular [3+2] nitrone cycloaddition.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/j.tet.2010.04.131DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040402010007131PublisherArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2924776/PubMed CentralArticle
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:Copyright © 2010 Elsevier. Received 1 March 2010; Received in revised form 21 April 2010; Accepted 29 April 2010; Available online 6 May 2010. 2009 Tetrahedron Prize for Creativity in Organic Chemistry. Dedicated to Professor Steven Ley, a friend and inspirational leader in organic chemistry. Funding from the NIH (1 RO1 CA 93591), Astellas (formerly Yamanouchi), Daiichi, and Fujisawa are gratefully acknowledged. MI thanks the University of Tokyo School of Agricultural Sciences. JLW thanks Amgen, Merck, Bristol-Myers Squibb, GlaxoSmithKline and Pfizer for research support. RNT would like to acknowledge the Jack and June Richardson Honors Scholarship Fund and the CSU CNS Undergraduate Scholarship Fund for financial support. Dr. Chris Incarvito, Dr. Chris Rithner, Don Heyse and Don Dick are acknowledged for their assistance with X-ray crystallography and instrumentation.
Funders:
Funding AgencyGrant Number
NIH1RO1CA93591
Astellas Foundation USAUNSPECIFIED
Daiichi Sankyo Co., Ltd.UNSPECIFIED
FujisawaUNSPECIFIED
University of Tokyo, School of Agricultural SciencesUNSPECIFIED
AmgenUNSPECIFIED
MerckUNSPECIFIED
Bristol-Myers SquibbUNSPECIFIED
GlaxoSmithKlineUNSPECIFIED
PfizerUNSPECIFIED
Jack and June Richardson Honors Scholarship FundUNSPECIFIED
Colorado State UniversityUNSPECIFIED
Subject Keywords:Welwitindolinone; [3+2] Dipolar cycloaddition; Rhodium carbenoid ;OeH insertion; Chloronium-ion semi-pinacol
Issue or Number:33
PubMed Central ID:PMC2924776
Record Number:CaltechAUTHORS:20141217-164835707
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20141217-164835707
Official Citation:David B. Freeman, Alexandra A. Holubec, Matthew W. Weiss, Julie A. Dixon, Akio Kakefuda, Masami Ohtsuka, Munenori Inoue, Rishi G. Vaswani, Hidenori Ohki, Brian D. Doan, Sarah E. Reisman, Brian M. Stoltz, Joshua J. Day, Ran N. Tao, Noah A. Dieterich, John L. Wood, Welwitindolinone C synthetic studies. Construction of the welwitindolinone carbon skeleton via a transannular nitrone cycloaddition, Tetrahedron, Volume 66, Issue 33, 14 August 2010, Pages 6647-6655, ISSN 0040-4020, http://dx.doi.org/10.1016/j.tet.2010.04.131. (http://www.sciencedirect.com/science/article/pii/S0040402010007131)
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:52995
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:18 Dec 2014 15:59
Last Modified:03 Oct 2019 07:46

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