title: A unified strategy for the asymmetric total syntheses of diversonol and lachnone C.
abstract: A unified synthetic strategy for the asymmetric syntheses of the natural products diversonol and lachnone C was developed by using the domino vinylogous aldol-oxa-Michael reaction as the enantioselective key step. Further transformations include dihydroxylation, lactol-opening by a Wittig-reaction, and lactonization. The obtained chromone lactones, a class of mycotoxins, can further be converted to tetrahydroxanthones by a Dieckmann condensation. This general method allows for the first time the enantioselective access to these classes of natural products and should be applicable to other members of the tetrahydroxanthone and chromone lactone families.
authors.affiliation: Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT) Campus South, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
authors.forename: Manuel C
authors.initials: MC
authors.lastname: Bröhmer
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Bourcet
authors.forename: Martin
authors.initials: M
authors.lastname: Nieger
authors.forename: Stefan
authors.initials: S
authors.lastname: Bräse
mesh_terms: D001203:Ascomycota / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002867:Chromones / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D044004:Xanthones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001688:Biological Products; D002867:Chromones; D007783:Lactones; D044004:Xanthones; C514121:diversonol; C570503:lachnone C