An Efficient Synthetic Method for (±)-Malyngolide and Its Optical Resolution
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概要
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A convenient synthetic method for (±)-malyngolide (1), an antibiotic from the marine blue-green alga Lyngbya majuscula GOMONT, is described. The compound (±)-1 was synthesized from 2-methylglutaric anhydride (starting material) in four steps, involving the TBHP-based osmiumcatalyzed procedure for vicinal dihydroxylation of the methylene unit in unsaturated carboxylic acid as the key step. The optical resolution of (±)-1 was accomplished by HPLC, in which diastereomeric (+)-2-(4-chlorophenyl)isovaleric acid [(+)-CPIA] esters of (±)-1 derived from (+)-CPIA-C1 could be easily separated, and subsequent hydrolysis of each ester gave the enantiomerically pure (-)-1 and (+)-1, respectively. A synthetic method for α-methylene malyngolide, which is to be expected for biological activity, is also described.
著者
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Kirihata Mitsunori
Department Of Agricultural Chemistry College Of Agriculture University Of Osaka Prefecture
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Ichimoto Itsuo
Department Of Agricultural Chemistry College Of Agriculture
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Ueda Hiroo
Department Of Agricultural Chemistry College Of Agriculture University Of Osaka Prefecture
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MACHIYA Kozo
Department of Agricultural Chemistry, College of Agriculture, University of Osaka Prefecture
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Machiya Kozo
Department Of Agricultural Chemistry College Of Agriculture University Of Osaka Prefecture:(present
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TONARI Kennosuke
Department of Agricultural Chemistry, College of Agriculture, University of Osaka Prefecture
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KIRIHATA Mitsunori
Department of Agricultual Chemistry, College of Agriculture, University of Osaka Prefecture
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