Improved synthesis of the ABCDE fragment of brevetoxin A.
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.
Crimmins
Michael T
MT
Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA. crimmins@email.unc.edu
McDougall
Patrick J
PJ
Ellis
J Michael
JM
D008387:Marine Toxins / Q000138:chemical synthesis*; D015394:Molecular Structure; D035964:Oxocins / Q000138:chemical synthesis*; D000095702:Polyether Toxins
D008387:Marine Toxins; D035964:Oxocins; C076262:Brevetoxin A; D000095702:Polyether Toxins