23 海産ポリエーテル化合物の絶対配置決定(口頭発表の部)

概要

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Marine polyether compounds have fascinated many scientists by their unique and complex structures and specific biological activities, as exemplified by the brevetoxins, the ciguatoxins, and maitotoxin. Although elucidation of the absolute stereochemistry of these compounds is essential for studying their mode of actions, biosynthesis, and chemical synthesis, difficulties existed due to their noncrystalline natures, and extremely limited availabilities. By applying anisotropic NMR reagents and chiral HPLC regeants, we successfully elucidated the absolute configuarations of pectenotoxin-6 (PTX6), dinophysistoxin-1 (DTX1), gambierol and gambieric acid. The absolute configurations of PTX6 and DTX1 were determined by preparing amides with anisotropic NMR reagents, (R)- and (S)-phenylglycine methyl esters (PGME). The axial C6-OH group in gambierol was converted to equatorial orientation and then esterified with (R)- and (S)-MTPA. NMR spectra of these esters indicated the absolute configuration at C6 to be S. The stereostrucures at C3, C9 and C48 in gambieric acid-B were determined by NMR measurements of its PGME amides and MTPA esters and by chiral HPLC analysis of an AP-OTf ester of an oxidative degradation product.
天然有機化合物討論会の論文
1998-08-31