99(P-14) 上水道臭気物質の合成と微生物分解(ポスター発表の部)

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Among the known methods for removing from drinking water the musty odour components, 2-methylisobomeol (1) and (-)-geosmin (2), which have frequently been generated, particularly in eutrophicated lakes, biodegradation with microorganisms is one of the most promising means. In contrast to numerous researches on the isolation and identification of the microorganisms capable of degrading 1 or 2, there are only a few reports on the structure of the degradation products of these compounds. We now present an investigation on the microbiological degradation of 1 and 2 with the back wash water collected from a biological filter of the pilot plant at Lake Biwa, and with the activated sludge obtained from Sendai City Sewerage Bureau. Some degradation products were detected and identified by GC, GC-MS and ^1H-NMR, and by the spectroscopic comparison with unambiguously synthesized authentic samples. These studies confirmed that both of 1 and 2 were first dehydrated to olefinic compounds and then oxidized gradually toward degradation. For these studies, we needed multi-gram quantities of pure 1 and 2. In order to access enatiomerically pure 2 with an extremely high overall yield, we developed a six-step process using a highly diastereoselective reduction of (+)-octalone 13 with DIBAL in tetrahydrofuran (THF) / 1,2-dimethoxyethane (DME), as the key reaction. We also demonstrated that the application of this reduction procedure to some other cyclic conjugated enones led to the corresponding allylic alcohols with high levels of diastereoselectivity and with high yields. Furthermore, we reported a method for the synthesis of 2 using an enzymatic kinetic resolution of racemic allylic alcohol (±)-14.
天然有機化合物討論会の論文
2000-10-01

99(P-14) 上水道臭気物質の合成と微生物分解(ポスター発表の部)

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