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- W2020508770 abstract "Kondensation von Zimtaldehyd (5) mit 2-Oxobuttersäure (6) liefert die (E,E)-Ketosäure 7, die nach Überführung in den Methylester 9 und Wittig-Reaktion mit (Methoxymethylen)triphenylphosphoran (9E)-Strobilurin A (1a) ergibt. Inversion der 9-Doppelbindung durch Belichten führt zu Strobilurin A (1b), das mit dem Naturprodukt identisch ist. Danach besitzen alle natürlichen Strobilurine 1b–4b im Gegensatz zu früheren Angaben die (9Z)-Konfiguration. Diese Zuordnung wird durch den spektroskopischen Vergleich von 1a und 1b sowie durch thermische Cyclisierung von 1b zum Biphenyl-Derivat 11 gesichert. 11 kann auch durch Reaktion von 2-(Methoxymethylen)acetessigsäure-methylester (13) mit Cinnamylidentriphenylphosphoran (12) erhalten werden. Kondensation von 13 unter basischen Bedingungen liefert 4-Hydroxyisophthalsäure-dimethylester (14). Antibiotics from Basidiomycetes, XX. – Synthesis of Strobilurin A and Revision of the Stereochemistry of Natural Strobilurins Condensation of cinnamaldehyde (5) with 2-oxobutyric acid (6) leads to the (E,E)-keto acid 7 which is converted into (9E)-strobilurin (1a) via methyl ester 9 and Wittig reaction of the latter with (methoxymethylene)triphenylphosphorane. On irradiation 1a undergoes inversion at the double bond in position 9 and yields strobilurin A (1b) which is identical with the natural product. Due to this result the (9Z) stereochemistry has to be assigned to all natural strobilurins 1b–4b, contrary to former formulations. This assignment is further supported by spectral comparison of 1a and 1b as well as by thermal cyclization of 1b to the biphenyl derivative 11. The latter can also be obtained by condensation of methyl 2-(methoxymethylene)acetoacetate (13) with cinnamylidenetriphenylphosphorane (12). Base-catalyzed condensation of 13 yields dimethyl 4-hydroxyisophthalate (14)." @default.
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- W2020508770 title "Antibiotika aus Basidiomyceten, XX Synthese von Strobilurin A und Revision der Stereochemie der natürlichen Strobilurine" @default.
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