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Ishii H, Niwaguchi T, Nakahara Y, Hayashi M.
“Studies on Lysergic Acid Diethylamide and Related Compounds. Part 8. Structural Identification of New Metabolites of Lysergic Acid Diethylamide obtained by Microbial Transformation using Streptomyces roseochromogenes”.
J.Chem.Soc. Perkin Trans.I. 1980;? (4):902-05.
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Abstract
A study of metabolites of lysergic acid diethylamide (LSD, I ) obtained by Streptomyces roseochromogenes is reported. Mycelium of S.roseochromogenes was suspended in soybean medium" preincubated at 28¡ then inoculated. A solution of (1) was added and incubation continued for 96-120 hr. The culture was added to EtOH then filtered, extracted with EtOAc then subjected to column chromatography yielding (5), (7) and (8). Structures were assigned from Et, NMR and MS data and chemical evidence. Treatment of lysergic acid (10) with (13) and triphenylphosphite imidazole complex gave (14). Treatment of (14) with HOAc yielded (8). Catalytic hydrogenation of (7) over PtO2 yielded (1) and (9). Treatment of (8) with AczO/py gave lysergic acid 2-acetoxyethyl ethylamide
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