P-2 海洋生物アメフラシ由来真菌が産生する細胞毒性天然物pericosine A-Dの合成研究(ポスター発表の部)

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Recently isolation of unique highly functionalized cyclohexenoid natural products designated pericosines A-E 1-5 as metabolites of Periconia byssoides OUPS-N133 originally separated from the sea hare, Aplysia kurodai, was reported. Among them pericosine A 1 showed remarkable inhibitory activity against the protein kinase EGFR and topoisomerase II in addition to in vivo antitumor activity against P388 cells. And the absolute stereostructure of pericosines A-C 1-3 had been elucidated by their total syntheses. However our successful first synthesis of pericosine A 1 was not satisfactory in the total yield. Here we disclose more effective second synthesis of (+)-1 via stereoselective ring opening of β-epoxide 11 derived from (-)-quinic acid 6. Syntheisi of (+)-pericosine C 3 from the same intermediate was also examined. On the other hand undefined absolute configuration of pericosine D 4 was elucidated by the short total synthesis via stereoselective ring opening of β-epoxide 15 assigned as methyl (3R,4R,5S,6R)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate. Using the same strategy, synthesis of (-)-pericosine B 2 was also accomplished.
2008-09-01