title: Total synthesis of brevetoxin A.
abstract: 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.
authors.affiliation: 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
authors.forename: Michael T
authors.initials: MT
authors.lastname: Crimmins
authors.forename: J Lucas
authors.initials: JL
authors.lastname: Zuccarello
authors.forename: J Michael
authors.initials: JM
authors.lastname: Ellis
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: McDougall
authors.forename: Pamela A
authors.initials: PA
authors.lastname: Haile
authors.forename: Jonathan D
authors.initials: JD
authors.lastname: Parrish
authors.forename: Kyle A
authors.initials: KA
authors.lastname: Emmitte
mesh_terms: 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
chemical_list: D000447:Aldehydes; D000475:Alkenes; D008387:Marine Toxins; D035964:Oxocins; C076262:Brevetoxin A; D000095702:Polyether Toxins