title: Total synthesis of alternariol.
abstract: Total synthesis of alternariol, a toxic secondary metabolite of various Alternaria fungi, was achieved in seven steps starting with orcinol and 3,5-dimethoxybromobenzene. The longest linear sequence consists of six steps. Key reaction is a palladium-catalyzed Suzuki-type coupling of an orcinol-derived boronic acid with a brominated resorcylic aldehyde. The final demethylation furnished alternariol in 73% yield containing a smaller fraction of alternariol 9-methyl ether (approximately 20%).
authors.affiliation: Institut für Organische Chemie, Universität Karlsruhe (TH), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
authors.forename: Karen
authors.initials: K
authors.lastname: Koch
authors.forename: Joachim
authors.initials: J
authors.lastname: Podlech
authors.forename: Erika
authors.initials: E
authors.lastname: Pfeiffer
authors.forename: Manfred
authors.initials: M
authors.lastname: Metzler
mesh_terms: D000528:Alternaria / Q000737:chemistry; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D009183:Mycotoxins / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry
chemical_list: D007783:Lactones; D009183:Mycotoxins; D010165:Palladium; C005197:alternariol