32 植物毒素コロナチンの不斉全合成とその生理活性(口頭発表の部)

概要

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Asymmetric synthesis of (+)-coronafacic (3) acid has been completed from (R)-(+)-4-acetoxy-2-cyclopenetene-1-one 29 as a chiral source. Construction of the 1-hydrindanone frame-work was carried out via intramolecular 1, 6-conjugate addition as the key step. Asymmetric synthesis of (+)-coronamic acid (4) and its possible three stereoisomers have been completed from (R)-malic acid 19 or (S)-malic acid as chiral sources. Construction of cyclopropane frame-work was carried out via dialkylation of dibenzyl malonate with cyclic sulfate by Sharpless's method. Coupling between (+)-coronafacic acid (3) and protected coronamic acid 26, and the subsequent deprotection provided (+)-coronatine(1). This is the first asymmetric total synthesis of (+)-coronatine(1). On several biological assay systems, coronatine (1) shows a 100 to 10,000 times higher activities than that of jasmonic acid (2). Coronafacic acid (3) is more structurally similar to jasmonic acid (2) than that of coronatine (1), however, coronafacic acid (3) shows slightly weaker activities than that of jasmonic acid(2). By using of coronatine (1), coronafacic acid (3), amino acid conjugated jasmonic acids and precursors of jasmonic acid biosynthesis, the study of biological activity is in progress.
天然有機化合物討論会の論文
1996-09-02