title: A convergent coupling strategy for the formation of polycyclic ethers: stereoselective synthesis of the BCDE fragment of brevetoxin A.
abstract: A stereoselective synthesis of the BCDE fragment of brevetoxin A has been completed. anti-Glycolate aldol, glycolate alkylation, and ring-closing metathesis reactions were employed as key bond-forming events. A convergent assembly strategy was employed that relied on a Horner-Wadsworth-Emmons union of two complex fragments. Subsequent cyclization and dehydration led to efficient generation of an intermediate endocyclic enol ether, which was advanced to a tetracyclic fragment. [reaction: see text]
authors.affiliation: Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA. crimmins@email.unc.edu
authors.forename: Michael T
authors.initials: MT
authors.lastname: Crimmins
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: McDougall
authors.forename: Kyle A
authors.initials: KA
authors.lastname: Emmitte
mesh_terms: D000478:Alkylation; D002384:Catalysis; D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D035964:Oxocins / Q000138:chemical synthesis* / Q000737:chemistry; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000095702:Polyether Toxins
chemical_list: D004988:Ethers, Cyclic; D008387:Marine Toxins; D035964:Oxocins; D011084:Polycyclic Aromatic Hydrocarbons; C076262:Brevetoxin A; D000095702:Polyether Toxins