title: A novel route to preussomerins via 2-arylacetal anions.
abstract: [reaction--see text] Dimerization of salicylaldehydes provided 6H,12H-6,12-epoxydibenzo[b, f][1,5]dioxocins in multigram quantities. Deprotonation-allylation of the benzylic acetals followed by further functionalization of the diallyl derivative and double Friedel-Crafts cyclization gave a novel preussomerin analogue which possessed the full carbon skeleton of the natural products.
authors.affiliation: Department of Chemistry, University of York, Heslington, York YO10 5DD, U.K.
authors.forename: J P
authors.initials: JP
authors.lastname: Ragot
authors.forename: M E
authors.initials: ME
authors.lastname: Prime
authors.forename: S J
authors.initials: SJ
authors.lastname: Archibald
authors.forename: R J
authors.initials: RJ
authors.lastname: Taylor
mesh_terms: D000080:Acetals / Q000737:chemistry; D019883:Alkyl and Aryl Transferases / Q000037:antagonists & inhibitors; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D001203:Ascomycota / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry; D005656:Fungal Proteins / Q000138:chemical synthesis / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000080:Acetals; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D004791:Enzyme Inhibitors; D004852:Epoxy Compounds; D005656:Fungal Proteins; D006576:Heterocyclic Compounds, 4 or More Rings; D013141:Spiro Compounds; D019883:Alkyl and Aryl Transferases; C064911:p21(ras) farnesyl-protein transferase