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- W2012308004 abstract "Der durch Diazomethan-Abbau von Desacetylanhydronaphthocyclinon-methylester (13) erhältliche 3,4,6,9-Tetrahydro-10-hydroxy-1-methyl-6,9-dioxo-1H-naphtho[2,3-c]pyran-3-essigsäuremethylester (6d) läßt sich über seinen Hydrochinon-monomethylether 10b oxidativ zu Didesoxyactinorhodin-dimethylester (8d) dimerisieren; dessen Cer(IV)-Hydroxylierung führt zu (1S,1′S,3R,3′R)-Actinorhodin (1c), dem Antipoden des von Actinomyces coelicolor gebildeten Chinon-Antibioticums, und bestätigt auf diesem Wege die 8,8′-Verknüpfung in 1a. Auf ähnliche Weise erhält man aus Nanaomycin A (7c) das Enantiomere 9c einer potentiellen Zwischenstufe der 1a-Biosynthese. Dimeric Naphthoquinones, XX. – Partial Synthesis of Actinorhodine Methyl 3,4-dihydro-9,10-dihydroxy-6-methoxy-1-methyl-1H-naphtho[2,3-c]pyran-3-acetate (10b), obtainable by diazomethane degradation of deacetylanhydronaphthocyclinone methyly ester (13) and monomethylation, is dimerised leading to dideoxyactinorhodine dimethyl ester (8d). Cer(IV) hydroxylation of the latter yields (1S,1′S,3R,3′R)-actinorhodine (1c), the enantiomer of the quinone antibiotic from Actinomyces coelicolor, thus confirming the 8,8′-connection in 1a. On a similar way, nanaomycin A (7c) gives 9c, the enantiomer of a potential intermediate of the biosynthesis of 1a." @default.
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- W2012308004 date "1987-04-27" @default.
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- W2012308004 title "Dimere Naphthochinone, XX. Partialsynthese von Actinorhodin" @default.
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- W2012308004 doi "https://doi.org/10.1002/jlac.198719870325" @default.
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