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Synlett 2012(2): 311-313  
DOI: 10.1055/s-0031-1290076
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthetic Approach to the Chemical Isostere of O-Methyl Honokiol

Minghua Cui, Hak Sung Kim*
Institute of Pharmaceutical Research and Development, College of Pharmacy, Wonkwang University, 344-2 Shinyong-Dong, Iksan, Jeonbuk 570-749, South Korea
Fax: +82(63)8431581; e-Mail: hankidad@wku.ac.kr;
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Publikationsverlauf

Received 19 September 2011
Publikationsdatum:
03. Januar 2012 (online)

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Abstract

We established a synthetic method for the chemical isostere of the structurally unique natural product, 4′-O-methyl honokiol by replacing two allyl groups with two different alkyl groups with the aim of developing synthetic analogues of the chemical isostere. The key steps in this synthetic route are the Suzuki-Miyaura coupling reaction for the formation of the phenylpyridine moiety and the Stille coupling reaction for the stepwise introduction of two allyl groups.

Key words

honokiol - 4′-O-methyl honokiol - chemical isostere - Suzuki-Miyaura coupling - Stille coupling

    References

  • 1 Konoshima T. Kozuka M. Tokuda H. Nishino H. Iwashima A. Haruna M. Ito K. Tanabe M. J. Nat. Prod.  1991,  54:  816 
    Suche in Google Scholar
  • 2a Esumi T. Makado G. Zhai H. Shimizu Y. Mitsumoto Y. Fukuyama Y. Bioorg. Med. Chem. Lett.  2004,  14:  2621 
    Suche in Google Scholar
  • 2b Lin Y.-R. Chen H.-H. Ko C.-H. Chan M.-H. Eur. J. Pharmacol.  2006,  537:  64 
    Suche in Google Scholar
  • 3 Nitao JK. Nair MG. Thorggood DL. Johnson KS. Scriber JM. Phytochemistry  1991,  30:  2193 
    Suche in Google Scholar
  • 4 Youn U.-J. Chen QC. Jin W.-Y. Lee I.-S. Kim H.-J. Lee J.-P. Chang M.-J. Min B.-S. Bae K.-H. J. Nat. Prod.  2007,  70:  1687 
    Suche in Google Scholar
  • 5 Oh JH. Kang LL. Ban JO. Kim YH. Kim KH. Han SB. Hong JT. Chem. Biol. Interact.  2009,  180:  506 
    Suche in Google Scholar
  • 6 Lee JW. Lee YK. Lee BJ. Nam S.-Y. Lee SI. Kim YH. Kim KH. Oh K.-W. Hong JT. Pharmacol. Biochem. Behav.  2010,  95:  35 
    Suche in Google Scholar
  • 7 Takeya T. Okubo T. Tobinaga S. Chem. Pharm. Bull.  1986,  34:  2066 
    Suche in Google Scholar
  • 8 Denton RM. Scragg JT. Galofré AM. Gui X.-C. Lewis W. Tetrahedron  2010,  66:  8029 
    Suche in Google Scholar
  • 9 Denton RM. Scragg JT. Saska J. Tetrahedron Lett.  2011,  52:  2554 
    Suche in Google Scholar
  • 10 Denton RM. Scragg JT. Synlett  2010,  633 
  • 11 Chen C.-M. Liu Y.-C. Tetrahedron Lett.  2009,  50:  1151 
    Suche in Google Scholar
  • 12 Angela M. Rodriguez JF. Sanz-Tejedor MA. Garcia-Ruano JL. Synlett  2003,  1678 
  • For recent reviews of Suzuki-Miyaura coupling, see:
  • 13a Suzuki A. Proc. Jpn. Acad., Ser. B.  2004,  80:  359 
    Suche in Google Scholar
  • 13b Kotha S. Lahiri K. Kashinath D. Tetrahedron  2002,  58:  9633 
    Suche in Google Scholar
  • 14a Cowart M. Faghih R. Curtis MP. Gfesser GA. Bennani YL. Black AL. Pan L. Marsh KC. Sullivan JP. Esbenshade TA. Fox GB. Hancock AA. J. Med. Chem.  2005,  48:  38 
    Suche in Google Scholar
  • 14b Pu Y.-M. Grieme T. Gupta A. Plata D. Bhatia AV. Cowart M. Ku Y.-Y. Org. Process Res. Dev.  2005,  9:  45 
    Suche in Google Scholar
  • 15 Sy W.-W. Tetrahedron Lett.  1993,  34:  6223 
    Suche in Google Scholar
  • 16a Heguaburu V. Mandolesi Sa M. Schapiro V. Pandolfi E. Tetrahedron Lett.  2008,  49:  6787 
    Suche in Google Scholar
  • 16b Vaz B. Alvarez R. R. de Lera A. J. Org. Chem.  2002,  67:  5040 
    Suche in Google Scholar
  • 16c Hoyt SB. London C. Park M. Tetrahedron Lett.  2009,  50:  1911 
    Suche in Google Scholar
  • 17 Fletcher S. Gunning PT. Tetrahedron Lett.  2008,  49:  4817 
    Suche in Google Scholar
  • 18 Anbazhagan M. Boykin DW. Stephens CE. Tetrahedron Lett.  2002,  44:  9089 
    Suche in Google Scholar
  • 19 Arnauld T. Barrett AGM. Hopkins BT. Tetrahedron Lett.  2002,  43:  1082 
    Suche in Google Scholar
  • 20 Alonso E. Guizarro D. Yus M. Tetrahedron  1995,  51:  11457 
    Suche in Google Scholar