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Synthesis 2009(13): 2146-2154  
DOI: 10.1055/s-0029-1216842
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient and General Preparation of Pyranostilbenes: First Total Synthesis of Artocarbene and Pawhuskin B

Byung Ho Parka, Yong Rok Lee*a, Won Seok Lyoob
a School of Chemical Engineering and Technology, Yeungnam University, Gyeongsan 712-749, Korea
b School of Textiles, Yeungnam University, Gyeongsan 712-749, Korea
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Publikationsverlauf

Received 14 January 2009
Publikationsdatum:
25. Mai 2009 (online)

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Abstract

An efficient and general synthesis providing pyranostilbenes in moderate yields has been developed. It consists of the reaction of pinosylvin with the appropriate α,β-unsaturated aldehyde catalyzed by ethylenediamine diacetate. As an application of this methodology, biologically active natural products artocarbene and pawhuskin B were synthesized by a convergent sequence from commercially available aldehydes.

Key words

heterocycles - alkenes - phenols - artocarbene - pawhuskin B

    References

  • 1a Nicolaou KC. Pfefferkorn JA. Roecker AJ. Cao G.-Q. Barluenga S. Mitchell HJ. J. Am. Chem. Soc.  2000,  122:  9939 
    Google Scholar
  • 1b Nicolaou KC. Pfefferkorn JA. Mitchell HJ. Roecker AJ. Cao G.-Q. Affleck RL. Lillig JE. J. Am. Chem. Soc.  2000,  122:  9954 
    Google Scholar
  • 1c Nicolaou KC. Pfefferkorn JA. Barluenga S. Mitchell HJ. Roecker AJ. Cao G.-Q. J. Am. Chem. Soc.  2000,  122:  9968 
    Google Scholar
  • 2a Atwal KS. Grover GJ. Ahmed SZ. Ferrara FN. Harper TW. Kim KS. Sleph PG. Dzwonczyk S. Russell AD. Moreland S. McCullough JR. Normandin DE. J. Med. Chem.  1993,  36:  3971 
    Google Scholar
  • 2b Evans JM. Fake CS. Hamilton TC. Poyser RH. Watts EA. J. Med. Chem.  1983,  26:  1582 
    Google Scholar
  • 2c Cassidy F. Evans JM. Hadley MS. Haladij AH. Leach PE. Stemp G. J. Med. Chem.  1992,  35:  1623 
    Google Scholar
  • 2d Gericke R. Harting J. Lues I. Schittenhelm C. J. Med. Chem.  1991,  34:  3074 
    Google Scholar
  • 2e Bergmann R. Gericke R. J. Med. Chem.  1990,  33:  492 
    Google Scholar
  • 2f Atwal KS. Grover GJ. Ferrara FN. Ahmed SZ. Sleph PG. Dzwonczyk S. Normandin DE. J. Med. Chem.  1995,  38:  1966 
    Google Scholar
  • 2g Elomri A. Mitaku S. Michel S. Skaltsounis A.-L. Tillequin F. Koch M. Pierré A. Guilbaud N. Léonce S. Kraus-Berthier L. Rolland Y. Atass G. J. Med. Chem.  1996,  39:  4762 
    Google Scholar
  • 2h Schweizer E. E. Meeder-Nycz D. Chromenes, Chromanones, and Chromones, In The Chemistry of Heterocyclic Compounds   Ellis GP. Wiley; New York: 1977.  Chap. 2.
    Google Scholar
  • 3a Hepworth JD. In Comprehensive Heterocyclic Chemistry   Vol. 3:  Katritzky AR. Pergamon; New York: 1984.  p.737 
    Google Scholar
  • 3b Bigi F. Chesini L. Magi R. Sartori G. J. Org. Chem.  1999,  64:  1033 
    Google Scholar
  • 3c Nielsen SF. Olsen CE. Christensen SB. Tetrahedron  1997,  53:  5573 
    Google Scholar
  • 3d Dorta RL. Martín A. Suárez E. Betancor C. J. Org. Chem.  1997,  62:  2273 
    Google Scholar
  • 3e Henry GE. Jacobs H. Tetrahedron  2001,  57:  5335 
    Google Scholar
  • 3f Nguyen VTH. Langer P. Tetrahedron Lett.  2005,  46:  815 
    Google Scholar
  • 3g Trost BM. Shen HC. Dong L. Surivet J.-P. Sylvain C. J. Am. Chem. Soc.  2004,  126:  11966 
    Google Scholar
  • 4a Gorham J. Tori M. Asakawa Y. The Biochemistry of the Stilbenoids   Chapman & Hall; London: 1995. 
    Google Scholar
  • 4b He S. Wu B. Pan Y. Jiang L. J. Org. Chem.  2008,  73:  5233 
    Google Scholar
  • 4c Ito T. Tanaka T. Linuma M. Iliya I. Nakaya K. Ali Z. Takahashi Y. Sawa R. Shirataki Y. Murata J. Dardaedi D. Tetrahedron  2003,  59:  5347 
    Google Scholar
  • 4d Sotheeswaran S. Pasupathy V. Phytochemistry  1993,  32:  1083 
    Google Scholar
  • 4e Seo E.-K. Chai H. Constant HL. Santisul T. Reutrakul V. Beecher CWW. Farnsworth NR. Cordell GA. Pezzuto JM. Kinghorn AD. J. Org. Chem.  1999,  64:  6976 
    Google Scholar
  • 4f Dai J.-R. Hallockm YF. Cardellina JHII. Boyd MR. J. Nat. Prod.  1998,  61:  351 
    Google Scholar
  • 5 Ali MA. Kondo K. Tsuda Y. Chem. Pharm. Bull.  1992,  40:  1130 
    CrossrefGoogle Scholar
  • 6 Boonlaksiri C. Onnanant W. Kongsaeree P. Kittakoop M. Tanticharoen Y. Thebtaranonth Y. Phytochemistry  2000,  54:  415 
    CrossrefPubMedGoogle Scholar
  • 7a Matsuda H. Morikawa T. Toguchida I. Park JY. Harima S. Yoshikawa M. Bioorg. Med. Chem.  2001,  9:  41 
    Google Scholar
  • 7b Fang J. Lu M. Chen J. Zhu H. Yang L. Wu L. Liu J. Chem. Eur. J.  2002,  8:  4191 
    Google Scholar
  • 8 Zheng JB. Ramirez VD. Biochem. Biophys. Res. Commun.  1999,  261:  499 
    CrossrefPubMedGoogle Scholar
  • 9a Orsini F. Pelizzoni F. Verotta L. Aburjai T. J. Nat. Prod.  1977,  60:  1082 
    Google Scholar
  • 9b Aburjai TA. Phytochemistry  2000,  55:  407 
    Google Scholar
  • 10 Yang LM. Lin SJ. Hsu FL. Yang TH. Bioorg. Med. Chem. Lett.  2002,  12:  1013 
    CrossrefPubMedGoogle Scholar
  • 11a Wang X. Heredia A. Song H. Zhang Z. Yu B. Davis C. Redfield R. J. Pharm. Sci.  2004,  93:  2448 
    Google Scholar
  • 11b Likhitwitayawuid K. Sritularak B. Benchanak K. Lipipun V. Mathew J. Schinazi RF. Nat. Prod. Res.  2005,  19:  177 
    Google Scholar
  • 12 Thakkar K. Geahlen RL. Cushman M. J. Med. Chem.  1993,  36:  2950 
    CrossrefPubMedGoogle Scholar
  • 13 Huang KS. Lin M. Yu LN. Kong M. Tetrahedron  2000,  56:  1321 
    CrossrefGoogle Scholar
  • 14 Uenobe F. Nakamura S. Miyazawa M. Mutat. Res.  1997,  373:  197 
    CrossrefPubMedGoogle Scholar
  • 15 Bokel M. Diyasena C. Gunatilaka AAL. Kraus W. Sotheeswaran S. Phytochemistry  1988,  27:  377 
    CrossrefGoogle Scholar
  • 16 Oshima Y. Namao K. Kamijou A. Matsuoka S. Nakano M. Terao K. Ohizumi Y. Experimentia  1995,  51:  63 
    CrossrefGoogle Scholar
  • 17 Shimizu K. Kondo R. Sakai K. Phytochemistry  1997,  45:  1297 
    CrossrefGoogle Scholar
  • 18 Shimizu K. Kondo R. Sakai K. Planta Med.  2000,  66:  11 
    Artikel in Thieme ConnectPubMedGoogle Scholar
  • 19 Belofsky G. French AN. Wallace DR. Dodson SL. J. Nat. Prod.  2004,  67:  26 
    CrossrefPubMedGoogle Scholar
  • 20 Neighbors JD. Salnikova MS. Wiemer DF. Tetrahedron Lett.  2005,  46:  1321 
    CrossrefGoogle Scholar
  • 21 Fang N. Casida J. J. Nat. Prod.  1999,  62:  205 
    CrossrefPubMedGoogle Scholar
  • 22a Lee YR. Choi JH. Yoon SH. Tetrahedron Lett.  2005,  46:  7539 
    Google Scholar
  • 22b Lee YR. Lee WK. Noh SK. Lyoo WS. Synthesis  2006,  853 
    Google Scholar
  • 22c Lee YR. Kim DH. Synthesis  2006,  603 
    Google Scholar
  • 22d Wang X. Lee YR. Tetrahedron Lett.  2007,  48:  6275 
    Google Scholar
  • 22e Wang X. Lee YR. Synthesis  2007,  3044 
    Google Scholar
  • 22f Lee YR. Xia L. Synthesis  2007,  3240 
    Google Scholar
  • 22g Lee YR. Kim JH. Synlett  2007,  2232 
    Google Scholar
  • 22h Lee YR. Li X. Kim JH. J. Org. Chem.  2008,  73:  4313 
    Google Scholar
  • 22i Lee YR. Xia L. Tetrahedron Lett.  2008,  49:  3283 
    Google Scholar
  • 22j Xia L. Lee YR. Synlett  2008,  1643 
    Google Scholar
  • 22k Lee YR. Hung TV. Tetrahedron  2008,  64:  7338 
    Google Scholar
  • 23 Hua S.-Z. Wang X.-B. Luo J.-G. Wang J.-S. Kong L.-Y. Tetrahedron Lett.  2008,  49:  5658 
    CrossrefGoogle Scholar
  • 24 Smith T. Modarelli DA. Tetrahedron Lett.  2008,  49:  526 
    CrossrefGoogle Scholar