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Journal of Wood Science

Official Journal of the Japan Wood Research Society

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Synthesis of isoacteoside, a dihydroxyphenylethyl glycoside

Journal of Wood Science volume 48, pages 512–515 (2002)Cite this article

Abstract

The total chemical synthesis of isoacteoside (1), 2-(3′,4′-dihydroxyphenyl)ethyl 6-O-caffeoyl-3-O-(α-l-rhamnopyranosyl)-β-d-glucopyranoside, is described. An acteoside acetate with benzyl groups at the catechols (3: 2-(3′,4′-dibenzyloxyphenyl)ethyl 2,6-di-O-acetyl-4-O-[3′,4′-bis(O-benzyl)caffeoyl]-3-O-(α-l-rhamnopyranosyl)-β-d-glucopyranoside) was treated with a solution of methy-lamine in methanol (MeNH2 in MeOH) to perform both deacetylation and caffeoyl migration, affording an isoacteoside derivative with benzyl groups at the catechols4b: 2-(3′,4′-dibenzyloxyphenyl)ethyl 6-O-[3′,4′-bis(O-benzyl) caffeoyl] -3-O-(α-l-rhamnopyranosyl)-β-d-glucopyranoside —in 34% yield. Debenzylation of4b was successfully accomplished by catalytic transfer hydrogenation using 1,4-cyclohexadiene to give the target compound isoacteoside (1) in 54% yield.1H and13C nuclear magnetic resonance spectral data of the synthesized isoacteoside (1) were identical with those of the natural isoacteoside isolated fromPaulownia tomentosa (Thumb.) Steud.

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Author notes

  1. Kozo Makino

    Present address: Human Technology Division, Eastern Hiroshima Prefecture Industrial Research Institute, Fukuyama, 721-0975, Hiroshima, Japan

Authors and Affiliations

  1. Faculty of Agriculture, Tottori University, 4-101 Minami, Koyama, 680-0945, Tottori, Japan

    Toshinari Kawada, Ryuji Asano, Kozo Makino & Tomoyasu Sakuno

Authors
  1. Toshinari Kawada
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  2. Ryuji Asano
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  3. Kozo Makino
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  4. Tomoyasu Sakuno
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Correspondence to Toshinari Kawada.

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Kawada, T., Asano, R., Makino, K. et al. Synthesis of isoacteoside, a dihydroxyphenylethyl glycoside. J Wood Sci 48, 512–515 (2002). https://doi.org/10.1007/BF00766648

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