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

Creators: Freeman, David B.; Holubec, Alexandra A.; Weiss, Matthew W.; Dixon, Julia A.; Kakefuda, Akio; Ohtsuka, Masami; Inoue, Munenori; Vaswani, Rishi G.; Ohki, Hidenori; Doan, Brian D.; Reisman, Sarah E.; Stoltz, Brian M.; Day, Joshua J.; Tao, Ran N.; Dieterich, Noah A.; Wood, John L.

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.

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.

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