Stereoselective Synthesis of Quaternary Carbons via the Dianionic Ireland-Claisen Rearrangement: An Approach to the Synthesis of Briarane Diterpenes Public Deposited

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Last Modified
  • March 21, 2019
Creator
  • Williams, Philip S.
    • Affiliation: College of Arts and Sciences, Department of Chemistry
Abstract
  • Investigation of the dianionic Ireland-Claisen rearrangement has led to the development of a simple method to enantioselectively access quaternary carbon stereocenters via a chelated transition state. This methodology was taken and applied to the synthesis of the core structure of Brianthein A. Peripheral modification of the core structure to complete the total synthesis proved quite challenging and ultimately was unsuccessful in forming the fused butenolide. This work represents the most advanced synthesis of brianthein A to date.
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  • In Copyright
Advisor
  • Crimmins, Michael T.
Degree
  • Doctor of Philosophy
Degree granting institution
  • University of North Carolina at Chapel Hill
Graduation year
  • 2012
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