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Author Notes:

Correspondence: Albert Padwa, Tel.: +1 404 727 0283; Fax: +1 404 727 6629;Email: chemap@emory.edu

Acknowledgments: We thank Dr. Jerremey Willis for some experimental assistance.


Research Funding:

We greatly appreciate the financial support provided by the National Science Foundation (CHE-0450779).


  • diterpene
  • icetexane
  • komaroviquinone
  • diazo carbonyl
  • rhodium(II)
  • catalyst
  • carbonyl ylide
  • intramolecular
  • dipolar-cycloaddition

A Rh(II)-catalyzed cycloaddition approach towards the synthesis of komaroviquinone


Journal Title:



Volume 64, Number 21


, Pages 4758-4767

Type of Work:

Article | Post-print: After Peer Review


Using a rhodium(II)-catalyzed cyclization/cycloaddition sequence as the key reaction step, the icetexane core of komaroviquinone was constructed by an intramolecular dipolar-cycloaddition of a carbonyl ylide dipole across a tethered π-bond. The ylide was arrived at by cyclization of a rhodium carbenoid intermediate onto a proximal ester group. Efforts towards the preparation of the required precursor for elaboration to the natural product are discussed.

Copyright information:

© 2008 Elsevier Ltd. All rights reserved.

This is an Open Access work distributed under the terms of the Creative Commons Attribution-NonCommerical-NoDerivs 3.0 Unported License (http://creativecommons.org/licenses/by-nc-nd/3.0/).

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