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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.
Subject:
Research Funding:
We greatly appreciate the financial support provided by the National Science Foundation (CHE-0450779).
Keywords:
- diterpene
- icetexane
- komaroviquinone
- diazo carbonyl
- rhodium(II)
- catalyst
- carbonyl ylide
- intramolecular
- dipolar-cycloaddition
A Rh(II)-catalyzed cycloaddition approach towards the synthesis of komaroviquinone
Abstract:
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/).
