Total synthesis of brevetoxin A.
A total synthesis of brevetoxin A is reported. Two tetracyclic coupling partners, prepared from previously reported advanced fragments, were effectively united via a Horner-Wittig olefination. The resulting octacycle was progressed to substrates that were explored for reductive etherification, the success of which led to a penultimate tetraol intermediate. The tetraol was converted to the natural product through an expeditious selective oxidative process followed by methylenation.
Crimmins
Michael T
MT
Department of Chemistry, Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA. crimmins@email.unc.edu
Zuccarello
J Lucas
JL
Ellis
J Michael
JM
McDougall
Patrick J
PJ
Haile
Pamela A
PA
Parrish
Jonathan D
JD
Emmitte
Kyle A
KA
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D035964:Oxocins / Q000138:chemical synthesis* / Q000737:chemistry; D013379:Substrate Specificity; D000095702:Polyether Toxins
D000447:Aldehydes; D000475:Alkenes; D008387:Marine Toxins; D035964:Oxocins; C076262:Brevetoxin A; D000095702:Polyether Toxins