A Stereocontrolled Synthesis of δ-trans-Tocotrienoloic Acid

David J. Maloney and Sidney M. Hecht*
Departments of Chemistry and Biology, University of Virginia, Charlottesville, Virginia 22901
Org. Lett., 2005, 7 (19), pp 4297–4300
DOI: 10.1021/ol051849t
Publication Date (Web): August 20, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sidhecht@virginia.edu

Abstract

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A consise stereoselective total synthesis of a naturally occurring polymerase β inhibitor, δ-trans-tocotrienoloic acid (2), is described. The key step in the synthesis is an acid-catalyzed cyclodehydration reaction. Additionally, this report corrects a previously reported structural assignment, defines the absolute stereochemistry of 2, and defines key structural requirements for polymerase β inhibition.

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History

  • Published In Issue September 15, 2005
  • Received August 2, 2005

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