Improved Synthesis of the ABCDE
Fragment of Brevetoxin A
Michael T. Crimmins,*Patrick J. McDougall, andJ. Michael Ellis
Venable and Kenan Laboratories of Chemistry, University of North Carolina at
Chapel Hill, Chapel Hill, North Carolina 27599
crimmins@email.unc.edu
Received June 27, 2006
Abstract:
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.
