title: Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A.
abstract: [reaction: see text] A stereoselective synthesis of the GHIJ fragment of brevetoxin A utilizing a convergent assembly strategy is described. Glycolate alkylation, ring-closing metathesis, and Hosomi-Sakurai reactions were central operations in the construction of the G ring and J ring subunits, which were united through a Horner-Wadsworth-Emmons coupling. Subsequent dehydrative cyclization produced an endocyclic enol ether that was further elaborated to the tetracyclic GHIJ fragment of brevetoxin A.
authors.affiliation: Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, 27599, 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: Pamela A
authors.initials: PA
authors.lastname: Cleary
authors.forename: Jonathan D
authors.initials: JD
authors.lastname: Parrish
mesh_terms: D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D035964:Oxocins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000095702:Polyether Toxins
chemical_list: D008387:Marine Toxins; D035964:Oxocins; C076262:Brevetoxin A; D000095702:Polyether Toxins