Towards the Total Synthesis
of 3-Hydroxyvibsanin E

Brett D. Schwartz; Justin R. Denton; Paul V. Bernhardt; Huw M. L. Davies; Craig M. Williams

doi:10.1055/s-0029-1216912

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Synthesis 2009(17): 2840-2846
DOI: 10.1055/s-0029-1216912

PAPER

Towards the Total Synthesis of 3-Hydroxyvibsanin E

Brett D. Schwartz^a, Justin R. Denton^b, Paul V. Bernhardt^a, Huw M. L. Davies*^c, Craig M. Williams*^a
^a School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane 4072, Queensland, Australia
Fax: +61(7)33654299; e-Mail: c.williams3@uq.edu.au;
^b Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY 14260-3000, USA
^c Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, GA 30322, USA
Fax: +1(404)7277766; e-Mail: hmdavie@emory.edu;

Further Information

Publication History

Received 26 June 2009
Publication Date:
23 July 2009 (online)

Abstract
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Abstract

The synthesis of a silyl-protected derivative of 3-hydroxyvibsanin E has been achieved. The key step is a regio- and stereoselective C-H hydroxylation of an advanced tricyclic intermediate by means of a Rubottom oxidation.

Key words

hydroxyvibsanin E - C-H hydroxylation - Rubottom oxidation

References

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Crystallographic data for structures 24, 26, and 27 have been deposited with the Cambridge Crystallographic Data Centre (CCDC 737635-737637) and may be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html, or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033, or e-mail: deposit@ccdc.cam.ac.uk.