Total synthesis of alternariol.
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%).
Koch
Karen
K
Institut für Organische Chemie, Universität Karlsruhe (TH), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
Podlech
Joachim
J
Pfeiffer
Erika
E
Metzler
Manfred
M
D000528:Alternaria / Q000737:chemistry; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D009183:Mycotoxins / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry
D007783:Lactones; D009183:Mycotoxins; D010165:Palladium; C005197:alternariol