Download PDF
Synlett 2020; 31(18): 1809-1812
DOI: 10.1055/s-0040-1707257
letter

Regioselective Biomimetic Synthesis of Dimeric Oxyresveratrol Derivatives

Lu Ran
,
Hongpeng Li
,
Ge Chao
,
Xiaodong Kang
,
Tian Lei
,
Wenling Li∗
School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, P. R. of China
› Author AffiliationsThis research work was financially supported by the National Natural Science Foundation of China (No. 21462024).
› Further Information
    Permissions and Reprints All articles of this category


Abstract

Oxyresveratrol and its methylated derivative as coupling precursors were efficiently prepared in four steps, with Wittig reactions and subsequent isomerization reactions as the key steps. The coupling reactions of oxyresveratrol under various oxidative conditions gave a complex and inseparable mixture of coupling products. The oxidative dimerizations of methylated oxyresveratrols catalyzed by horseradish peroxidase–H2O2 or FeCl3·6H2O in an acetone system predominantly produced the 8–5-coupled and 8–10-coupled dihydrobenzofuran-type dimers, respectively. This regioselective biomimetic strategy might be useful in synthesizing other dimeric oxyresveratrol derivatives.

Key words

oxyresveratrol - biomimetic synthesis - oligostilbenes - oxidative coupling - dimerization - regioselectivity

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707257.
  • Supporting Information


Publication History

Received: 08 July 2020

Accepted: 03 August 2020

Article published online:
01 September 2020

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References and Notes

    • 1a Hu ST, Zheng ZP, Zhang XC, Chen F, Wang MF. J. Funct. Foods 2015; 13: 375
    • 1b Soekamtoa NH, Achmad SA, Ghisalberti EL, Hakim EH, Syah YM. Indones. J. Chem. 2005; 5: 207
    • 1c Xu L, Liu C, Xiang W, Chen H, Qin X, Huang X. Int. J. Pharmacol. 2014; 10: 44
    • 2a Aftaba N, Likhitwitayawuid K, Vieira A. Nat. Prod. Res. 2010; 24: 1726
      CrossrefPubMed
    • 2b Chatsumpun N, Chuanasa T, Sritularak B, Lipipun V, Jongbunprasert V, Ruchirawat S, Ploypradith P, Likhitwitayawuid K. Molecules 2016; 21: 489
      CrossrefPubMed
    • 2c Galindo I, Hernáez B, Berná J, Fenoll J, Cenis JL, Escribano JM, Alonso C. Antiviral Res. 2011; 91: 57
      CrossrefPubMed
    • 2d Mei M, Ruan J.-Q, Wu W.-J, Zhou R.-N, Lei JP.-C, Zhao H.-Y, Yan R, Wang Y.-T. J. Agric. Food Chem. 2012; 60: 2299
      CrossrefPubMed
    • 2e Likhitwitayawuid K, Sornsute A, Sritularak B, Ploypradith P. Bioorg. Med. Chem. Lett. 2006; 16: 5650
      CrossrefPubMed
    • 3a Likhitwitayawuid K, Sritularak B. J. Nat. Prod. 2001; 64: 1457
      CrossrefPubMed
    • 3b Choa HM, Haa TK. Q, Phama HT. T, Ana J.-P, Huha J, Leea B.-W, Leea HJ, Oh WK. Phytochemistry 2019; 165: 112044
      CrossrefPubMed
    • 3c Tanaka T, Iliya I, Ito T, Furusawa M, Nakaya K, Ionuma M, Shirataki Y, Matsuura N, Ubukata M, Murata J, Simozono F, Hirai K. Chem. Pharm. Bull. 2001; 49: 858
      CrossrefPubMed
    • 3d Li X.-m, Lin M, Wang Y.-h, Liu X. Planta Med. 2004; 70: 160
      Article in Thieme ConnectPubMed

      For reviews, see:
    • 4a Sotheeswaran S, Pasupathy V. Phytochemistry 1993; 32: 1083
      Crossref
    • 4b Lin M, Yao C.-S. Stud. Nat. Prod. Chem. 2006; 33: 601
    • 4c Shen T, Wang X.-N, Lou H.-X. Nat. Prod. Rep. 2009; 26: 916
      CrossrefPubMed
    • 4d Quideau S, Deffieux D, Douat-Casassus C, Pouységu L. Angew. Chem. Int. Ed. 2011; 50: 586
      CrossrefPubMed
    • 4e Snyder SA, ElSohly AM, Kontes F. Nat. Prod. Rep. 2011; 28: 897
      CrossrefPubMed
    • 4f Synder SA. Recent Adv. Polyphenol Res. 2012; 3: 311
    • 4g Velu SS, Thomas NF, Weber JF. Curr. Org. Chem. 2012; 16: 605
      Crossref
    • 4h Li WL, Zang P, Li HF, Yang SX. Prog. Chem. 2012; 24: 545
    • 4i Li W, Lv T, Yang Y, Yang Y. Youji Huaxue 2013; 33: 2443
    • 4j Keylor MH, Matsurra BS, Stephenson CR. J. Chem. Rev. 2015; 115: 8976
      Article in Thieme ConnectPubMed
    • 4k Wang X.-F, Yao C.-S. J. Asian Nat. Prod. Res. 2016; 18: 376
      CrossrefPubMed
  • 5 Li Z, Kang S, Chen L, Wang Y, Li J. Youji Huaxue 2016; 36: 1143
    • 6a Sun H.-Y, Xiao C.-F, Wei W, Chen Y, Lü Z.-L, Zou Y. Youji Huaxue 2010; 30: 1574
    • 6b Sun H.-Y, Xiao C.-F, Cai Y.-C, Chen Y, Wei W, Liu X.-K, Lv Z.-L, Zou Y. Chem. Pharm. Bull. 2010; 58: 1492
      CrossrefPubMed
    • 7a Lee SK, Nam KA, Hoe YH, Min H.-Y, Kim E.-Y, Ko H, Song S, Lee T, Kim S. Arch. Pharm. Res. 2003; 26: 253
      CrossrefPubMed
    • 7b Reimann E. Tetrahedron Lett. 1970; 4051
    • 8a Bates RB, Caldera S, Deshpande VH, Malik BL, Paknikar SK. J. Nat. Prod. 1997; 60: 1041
      Crossref
    • 8b Alesso EN, Finkielsztein LM, Lantaño B, Aguirre JM, Iglesias GY. M. J. Chem. Res., Synop. 1999; 23: 302
      Crossref
    • 9a Li W, Li H, Luo Y, Yang Y, Wang N. Synlett 2010; 1247
    • 9b Li W, Luo Y, Li H, Zang P, Han X. Synthesis 2010; 3822
    • 9c Li W, Yang S, Lv T, Yang Y. Org. Biomol. Chem. 2014; 12: 2273
      CrossrefPubMed
    • 9d Yang Y, Liu Q, Chen P, Li W. Tetrahedron Lett. 2014; 55: 4455
      Crossref
    • 9e Li W, Chen P, Yang Y, Liu X, Dong T. Tetrahedron 2016; 72: 210
      Crossref
    • 9f Li W, Dong T, Chen PL, Liu X, Liu M, Han X. Tetrahedron 2017; 73: 3056
      Crossref
    • 9g Liu M, Guan X, Shao Z, Li W. Tetrahedron 2018; 74: 4013
      Crossref
    • 9h Guan X, Liu M, Shao Z, Li H, Ran L, Li W. Synthesis 2019; 51: 1825
      Article in Thieme Connect
  • 10 Li W, Li H, Li Y, Hou Z. Angew. Chem. Int. Ed. 2006; 45: 7609
    CrossrefPubMed
  • 11 Yu J, Gaunt MJ, Spencer JB. J. Org. Chem. 2002; 67: 4627
    CrossrefPubMed
  • 12 Alonso F, Riente P, Yus M. Eur. J. Org. Chem. 2009; 34: 6034
    • 13a Correa A, Mancheño O G, Bolm C. Chem. Soc. Rev. 2008; 37: 1108
      CrossrefPubMed
    • 13b Bauer I, Knölker H.-J. Chem. Rev. 2015; 115: 3170
      CrossrefPubMed
  • 14 5-[(E)-2-(4-Hydroxy-2-methoxyphenyl)ethenyl]benzene-1,3-diol [(E)-15] Pale-yellow oil; yield: 1.77 g (91%). 1H NMR (500 MHz, acetone-d 6): δ = 3.85 (s, 3 H), 6.24 (t, J = 2.0 Hz, 1 H), 6.46 (dd, J = 8.5, 2.0 Hz, 1 H), 6.49 (d, J = 2.0 Hz, 1 H), 6.52 (d, J = 2.0 Hz, 2 H), 6.88 (d, J = 16.5 Hz, 1 H), 7.30 (d, J = 16.5 Hz, 1 H), 7.45 (d, J = 8.5 Hz, 1 H), 8.16 (br s, 2 H), 8.51 (br s, 1 H). 13C NMR (125 MHz, acetone-d 6): δ = 55.8, 99.8, 99.9, 102.4, 105.5 (2 C), 108.5, 118.7, 123.9, 126.8, 127.9, 141.5, 159.2, 159.5, 159.6. HRMS (ESI): m/z [M –H]+ calcd for C15H13O4: 257.08193; found: 257.08191.
  • 15 5-{(E)-2-[3-(3,5-Dihydroxyphenyl)-2-(4-hydroxy-2-methoxyphenyl)-6-methoxy-2,3-dihydro-1-benzofuran-5-yl]ethenyl}benzene-1,3-diol (16) Yellowish amorphous powder; yield: 31 mg (62%). 1H NMR (500 MHz, acetone-d 6): δ = 3.77 (s, 3 H), 3.94 (s, 3 H), 4.36 (d, J = 5.0 Hz, 1 H), 5.73 (d, J = 5.0 Hz, 1 H), 6.21 (d, J = 2.0 Hz, 2 H), 6.23 (t, J = 2.0 Hz, 1 H), 6.24 (t, J = 2.0 Hz, 1 H), 6.40 (dd, J = 8.5, 2.0 Hz, 1 H), 6.50 (d, J = 2.0 Hz, 2 H), 6.52 (d, J = 2.0 Hz, 1 H), 6.64 (d, J = 2.0 Hz, 1 H), 6.84 (d, J = 16.5 Hz, 1 H), 7.12 (d, J = 8.5 Hz, 1 H), 7.32 (d, J = 2.0 Hz, 1 H), 7.35 (d, J = 16.5 Hz, 1 H), 8.15 (br s, 2 H), 8.16 (br s, 2 H), 8.46 (br s, 1 H). 13C NMR (125 MHz, acetone-d 6): δ = 55.7, 56.2, 89.8, 94.3, 100.0, 102.0, 102.5, 105.5, 105.6 (2 C), 107.0, 107.1 (2 C), 107.6, 119.8, 121.2, 122.9 (2 C), 123.4, 123.9, 126.8, 128.1, 141.4, 147.2, 159.0, 159.1, 159.5, 159.6 (2 C), 162.2. HRMS (ESI): m/z [M – H]+ calcd for C30H25O8: 513.15549; found: 513.15547.
  • 16 5-{6-Hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-[(E)-2-(3-hydroxy-5-methoxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl}benzene-1,3-diol (18) Yellowish amorphous powder; yield: 15 mg (45%). 1H NMR (500 MHz, acetone-d 6): δ = 3.76 (s, 3 H), 3.83 (s, 3 H), 4.36 (d, J = 5.0 Hz, 1 H), 5.67 (d, J = 5.0 Hz, 1 H), 6.20 (dd, J = 8.5, 2.0 Hz, 1 H), 6.26 (d, J = 2.0 Hz, 2 H), 6.34 (dd, J = 8.0, 2.0 Hz, 1 H), 6.36 (d, J = 2.0 Hz, 2 H), 6.41 (d, J = 2.0 Hz, 1 H), 6.51 (d, J = 2.0 Hz, 1 H), 6.68 (d, J = 2.0 Hz, 1 H), 6.76 (d, J = 16.5 Hz, 1 H), 7.05 (d, J = 8.0 Hz, 1 H), 7.15 (d, J = 16.5 Hz, 1 H), 7.16 (d, J = 8.0 Hz, 1 H). 13C NMR (125 MHz, acetone-d 6): δ = 55.6, 55.7, 55.8, 89.1, 99.7, 99.8, 103.9, 107.0, 107.3, 108.3, 118.6, 120.1, 122.3, 123.8, 125.3, 125.6, 127.2, 127.8, 128.1, 128.4, 137.2, 148.1, 151.9, 158.5 (2 C), 159.3 (2 C), 159.5, 162.8 (2 C). HRMS (ESI): m/z [M – H]+ calcd for C30H25O8: 513.15549; found: 513.15546.