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Oxidative Spirocyclization of Phenolic Sulfonamides: Scope and Applications

  1. Huan Liang1,2,
  2. Prof. Dr. Marco A. Ciufolini1,*

Article first published online: 7 OCT 2010

DOI: 10.1002/chem.201001402

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 16, Issue 44, pages 13262–13270, November 22, 2010

Additional Information

How to Cite

Liang, H. and Ciufolini, M. A. (2010), Oxidative Spirocyclization of Phenolic Sulfonamides: Scope and Applications. Chem. Eur. J., 16: 13262–13270. doi: 10.1002/chem.201001402

Author Information

  1. 1

    Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1 (Canada), Fax: (+1)604-822-8710

  2. 2

    Current address: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138 (USA)

*Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1 (Canada), Fax: (+1)604-822-8710

Publication History

  1. Issue published online: 15 NOV 2010
  2. Article first published online: 7 OCT 2010
  3. Manuscript Received: 21 MAY 2010

Funded by

  • University of British Columbia
  • the Canada Research Chair Program
  • CFI
  • BCKDF
  • NSERC
  • CIHR
  • MerckFrosst Canada
  • UGF Fellowship
  • G.E. Laird Research Fellowship

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Keywords:

  • alkaloids;
  • dearomatization;
  • lepadiformine;
  • phenols;
  • sulfonamides

Abstract

A full account of the oxidative dearomatization of para- and ortho-phenolic sulfonamides is provided together with an overview of the chemistry of the products and their elaboration to building blocks for spirocyclic alkaloids. A concise total synthesis of putative lepadiformine complements the discussion.

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