P-60 抗HIV活性物質13-オキシインゲノールの合成研究(ポスター発表の部)  [in Japanese] P-60 Synthetic Study of 13-Oxyingenol(Poster Presentation)  [in Japanese]

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Abstract

13-Oxyingenol (1) and ingenol (2) are diterpenoids isolated from the plants of Euphorbia sp. They and their analogs have interesting bioactivities. Particularly, 13-oxyingenol derivatives such as RD4-2138 have a strong anti-HIV activity. The structural features of ingenol and 13-oxyingenol are a high degree of oxygenation and a highly strained inside-outside bicylcic ring system. The molecular complexity of ingenol derivatives, in conjunction with their potent biological activities, has made them attractive synthetic targets. We planed the synthesis of 13-oxyingenol (1) by using ring-closing olein metathesis strategy. The starting point for this work was the construction of the β-ketoester 3 from 2-(4-hydroxyphenyl)ethanol. We stereoselectively introduced the methyl group to C-11 by using diastereoselective hydrogenation, to give β-ketoester 3 with desired stereochemistry. Then, we achieved the construction of the full carbon framework of 13-oxyingenol by using intramolecular spirocyclization and ring closing olefin metathesis as key steps. Further approach to 13-oxyingenol is currently underway in our group and will be reported in the symposium.

Journal

  • Symposium on the Chemistry of Natural Products, symposium papers

    Symposium on the Chemistry of Natural Products, symposium papers 50(0), 719-724, 2008

    Symposium on the Chemistry of Natural Products Steering Committee

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