著者

Kozo MACHIYA Itsuo ICHIMOTO Kennosuke TONARI Mitsunori KIRIHATA Hiroo UEDA

出版者

Japan Society for Bioscience, Biotechnology, and Agrochemistry

雑誌

Agricultural and Biological Chemistry (ISSN:00021369)

巻号頁・発行日

vol.49, no.6, pp.1767-1773, 1985 (Released:2006-03-27)

参考文献数

12

被引用文献数

3

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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.