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- W2055368889 abstract "Aus der Mutterlauge der Phorbol-Darstellung wird eine mit Phorbol (1) isomere Verbindung 2 isoliert und aufgrund ihrer chemischen und spektroskopischen Eigenschaften als das 4α-Epimere von 1 (Isophorbol) identifiziert. 2 wird aus 1 durch Basen-katalysierte Epimerisierung erhalten. Die durch Basen katalysierte Acetylierung von 2 liefert, anders als jene von 1, neben 4α-Phorbol-12.13.20-triacetat (3) auch 4α-Phorbol-4.12.13.20-tetraacetat (5). Methylierung von 3 mit Methyljodid/Silberoxid in Dimethylformamid führt zu drei Methylierungsprodukten: 4-O-Methyl-4α-phorbol-12.13.20-triacetat(10), 4.13-Di-O-Methyl-4α-phorbol-12.20-diacetat (11) und 4-O-Methyl-4α-phorbol-12.20-diacetat (12). Reduktion von 3 mit Zink/Eisessig ergibt 4-Desoxy-4α-phorbol-12.13.20-triacetat (16). On the Chemistry of Phorbol, XVI. 4α-Phorbol From the mother liquor of preparations of phorbol (1) an isomer 2 (isophorbol) is isolated. Chemical and spectroscopic data reveal that 2 is 4α-phorbol. 2 is obtained from 1 by basecatalyzed epimerization. In contrast to phorbol, base-catalyzed acetylation of 2 yields both 4α-phorbol-12,13,20-triacetate (3) and 4α-phorbol-4,12,13,20-tetraacetate (5). By methylation of 3 with methyl iodide/silver oxide in dimethylformamide three products are obtained: 4-O-methyl-4α-phorbol-12,13,20-triacetate (10), 4,13-di-O-methyl-4α-phorbol-12,20-diacetate (12)and 4-O-methyl-4α-phorbol-12,20-diacetate (11). On reduction with zinc/acetic acid, 3 yields 4-deoxy-4α-phorbol-12,13,20-triacetate (16)." @default.
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- W2055368889 date "1970-11-30" @default.
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- W2055368889 title "Zur Chemie des Phorbols, XVI. 4α-Phorbol" @default.
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- W2055368889 doi "https://doi.org/10.1002/jlac.19707410103" @default.
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