Archives of Pharmacal Research

  • 제29권7호
  • /
  • Pages.563-565
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  • 2006
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  • 0253-6269(pISSN)
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  • 1976-3786(eISSN)
대한약학회 (The Pharmaceutical Society of Korea)
권호 표지

A Convenient Synthesis of an Anti-Helicobacter Pylori Agent, Dehydrodiconiferyl Alcohol

  • Hu, Kun (College of Pharmacy, Kyung Hee University) ;
  • Jeong, Jin-Hyun (College of Pharmacy, Kyung Hee University)
  • 발행 : 2006.07.01
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초록

Potential anti-Helicobacter pylori agent dehydrodiconiferyl alcohol was synthesized in 44% overall yield, starting from vanillin which could be commercially available. Carbon extension of vanillin followed by the Horner-Wadsworth-Emmons reaction, a biomolecular radical coupling reaction and DIBAL-H reduction gave dehydrodiconiferyl alcohol.

키워드

참고문헌

  1. Binns, A. N., Chen, R. H., Wood, H. N., and Lynn, D. G., Cell division promoting activity of naturally occurring dehydrodiconiferyl glucosides: Do cell wall components control cell division? Proc. Natl. Acad. Sci.U.S.A., 84, 980-984 (1987)
  2. Chai-Lin Kao and Ji-Wang Chern, A convenient synthesis of naturally occurring benzofuran ailanthoidol. Tetrahedron Lett., 42, 1111-1113 (2001) https://doi.org/10.1016/S0040-4039(00)02163-8
  3. Chai-Lin Kao and Ji-Wang Chern, A novel strategy for the synthesis of benzofuran skeleton neolignans: Application to ailanthoidol, XH-14, and obovaten. J. Org. Chem., 67, 6772- 6787 (2002) https://doi.org/10.1021/jo0258960
  4. Ezio Bolzacchini, Gosta Brunow, Simore Meinardi, Marco Orlandi, Bruno Rindone, Petteri Rummakko, and Harri Setala, Enantioselective synthesis of a benzofuranic neolignan by oxidation coupling. Tetrahedron Lett., 39, 3291-3294 (1998) https://doi.org/10.1016/S0040-4039(98)00473-0
  5. Fernandes, Eduarda G. R., Pinto, Madalena M. M., Silver, Artur M. S., Cavaleiro, Jose A. S., and Gottlieb, Otto R., Synthesis and structural Elucidation of Xanthonolignoids: trans-(${\pm}$)- Kielcorin B and trans-(${\pm}$)-Isokielcorin B., Heterocycles, 51, 821-828 (1999) https://doi.org/10.3987/COM-98-8371
  6. Freudenberg, K., Lignin: Its constitution and formation from phydroxycinnamyl alcohols. Science, 148, 595-600 (1965) https://doi.org/10.1126/science.148.3670.595
  7. Haikarainen, A., Sipila, J., Pietikainen, P., Pajunen, A., and Mutikainen, I., Salen complexes with bulky substituents as useful tools for biomimetic phenol oxidation research. Bioorg. Med. Chem., 9, 1633-1638 (2001) https://doi.org/10.1016/S0968-0896(01)00053-0
  8. John Ralph; Yinsheng Zhang. A new synthesis of (Z)-coniferyl alcohol, and characterization of its derived synthetic lignin. Tetrahedron, 54, 1349-1354 (1998) https://doi.org/10.1016/S0040-4020(97)10361-1
  9. Kaori Ando, Highly Selective Synthesis of Z-Unsaturated Esters by Using New Horner-Emmons Reagents, Ethyl (Diarylphosphono) acetates. J. Org. Chem., 62, 1934-1939 (1997) https://doi.org/10.1021/jo970057c
  10. Lemiere, G., Gao, M., De Groot, A., Domisse, R., Lepoivre, J., and Pieters, B., Perkin Trans.1, 3', 4-Di-O-methylcedrusin: synthesis, resolution and absolute configuration. J. Chem. Soc., 1775 (1995)
  11. Lewis, G. N. and Yamamoto, E. Annu, Lignin: occurrence, biogenesis and biodegradation. Rev. Plant Mol. Biol., 41,455- 496 (1990) https://doi.org/10.1146/annurev.pp.41.060190.002323
  12. Lynn, A. N., Chen, R. H., Manning, K. S., and Wood, H. N., The structural characterization of endogenous factors from Vinca rosea crown gall tumors that promote cell division of tabacco cells. Proc. Natl. Acad. Sci. U.S.A., 84,615-619 (1987)
  13. Marco Orlandi, Bruno Rindone, Giorgio Molteni, Petteri Rummakko, and Gosta Brunow, Asymmetric biomimetic oxidations of phenols: the mechanism of the diastereo- and enantioselective synthesis of dehydrodiconiferyl ferulate (DDF) and dehydrodiconiferyl alcohol (DDA). Tetrahedron, 57, 371-378 (2001) https://doi.org/10.1016/S0040-4020(00)00944-3
  14. Ochi, T., Takaishi, Y., Shibata, H., Higuti, T., and Kataoka, M., Chemical constituents of Capsicum annuum L var. angulosum, and anti Helicobacter pylori activity, Natural Medicines, 59, 76-84 (2005)
  15. Petteri Rummakko, Gosta Brunow, Marco Orlandi, and Bruno Rindone, Asymmetric biomimetic oxidations of phenols: enantioselective synthesis of (+)- and (-)-Dehydrodiconiferyl alcohol. Synlett, 3, 333-335 (1999)
  16. Quideau, S. and Ralph, J., A biomimetic route to lignin model compounds via Silver (I) oxide oxidation. Holzforshung, 48, 12 (1994) https://doi.org/10.1515/hfsg.1994.48.1.12
  17. Stephane Quideau and John Ralph, Facile large-scale synthesis of coniferyl, sinapyl, and p-coumaryl alcohol. J. Agric. Food Chem., 40, 1108-1110 (1992) https://doi.org/10.1021/jf00019a003
  18. Strehlke, P. and Kessler, H. J., European J. of Med. Chem., 14, 238-242 (1979)
  19. Syjanen, K. and Brunow, G., Oxidation cross coupling of phydroxycinnamic alcohols with dimeric arylglycerol ${\beta}$-aryl ether lignin model compounds. The effect of oxidation potentials. J. Chem. Soc. Perkin Trans., 1, 20, 3425-3430 (1998)
  20. Syrjanen, K. and Brunow, G., Regioselectivity in oxidative crosscoupling of phenols. Application to the synthesis of dimeric neolignans. Tetrahedron, 57, 365-370 (2001) https://doi.org/10.1016/S0040-4020(00)00943-1
  21. Takara, K., Kjnjyo, A., Matsui, D., Wada, K., Nakasone, Y., and Yogi, S., Antioxidative phenolic compounds from non-sugar fraction in kokuto, non-centrifugal cane sugar. Nippon Nogeikagaku Kaishi (in Japanese), 74, 885-890 (2000)