P-84 チオマリノールBの全合成研究(ポスター発表の部)

概要

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The polyketide derived marine natural product thiomarinols, isolated from the bacterium Alteromonas rava sp. nov. SANK 73390, were found to exhibit potent antimicrobial activity. We report here the total synthesis of thiomarinol A (1), which had been successfully converted to thiomarinol B (2) by Sankyo group. Diastereoselective construction of the tetrahydropyran moiety, a common structural unit of the thiomarinols, with four contiguous stereogenic centers was achieved efficiently employing the oxy-Michael reaction under both anionic and high-pressure conditions. After assembling the 4-hydroxymonic acid segment, it was condensed with the pyrrothin chromophore and the 7-hydroxyoctanoic acid moiety to provide the protected thiomarinol A (1), which was treated with hydrochloric acid to give thiomarinol A (1). Spectral properties of the synthetic thiomarinol A were identical with those for the natural product.
天然有機化合物討論会の論文
2008-09-01