Improved Synthesis of the ABCDE Fragment of Brevetoxin A

Michael T. Crimmins,* Patrick J. McDougall, and J. Michael Ellis
Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599
Org. Lett., 2006, 8 (18), pp 4079–4082
DOI: 10.1021/ol0615782
Publication Date (Web): August 4, 2006
Copyright © 2006 American Chemical Society

Abstract

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A second-generation synthesis of the BCDE fragment of brevetoxin A is described. Novel reactions were developed that extend the utility of the asymmetric glycolate alkylation reaction and improve scale-up to provide gram quantities of the B and E subunits. Significant improvements to the convergent assembly of the tetracycle were also realized. In addition, formation of the A ring lactone was accomplished to complete the ABCDE pentacycle.

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History

  • Published In Issue August 31, 2006
  • Received June 27, 2006

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