메뉴 건너뛰기




Volumn 18, Issue 4, 2013, Pages 4739-4765

Application of the Suzuki-Miyaura reaction in the synthesis of flavonoids

Author keywords

4 arylcoumarin; Biflavone; Chalcone; Flavone; Flavonoid; Isoflavone; Neoflavone; Suzuki Miyaura reaction

Indexed keywords

FLAVONOID;

EID: 84876771689     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18044739     Document Type: Review
Times cited : (88)

References (84)
  • 1
    • 14544305986 scopus 로고    scopus 로고
    • The first total synthesis of kwakhurin a characteristic component of a rejuvenating plant "kwao keur": Toward an efficient synthetic route to phytoestrogenic isoflavones
    • Ito, F.; Iwasaki, M.; Watanabe, T.; Ishikawa, T.; Higuchi, Y. The first total synthesis of kwakhurin, a characteristic component of a rejuvenating plant, "kwao keur": toward an efficient synthetic route to phytoestrogenic isoflavones. Org. Biomol. Chem. 2005, 3, 674-681.
    • (2005) Org. Biomol. Chem. , vol.3 , pp. 674-681
    • Ito, F.1    Iwasaki, M.2    Watanabe, T.3    Ishikawa, T.4    Higuchi, Y.5
  • 2
    • 77958558514 scopus 로고    scopus 로고
    • Total synthesis of the pyranoisoflavone kraussianone 1 and related isoflavones
    • Selepe, M.A.; Drewes, S.E.; van Heerden, F.R. Total synthesis of the pyranoisoflavone kraussianone 1 and related isoflavones. J. Nat. Prod. 2010, 73, 1680-1685.
    • (2010) J. Nat. Prod. , vol.73 , pp. 1680-1685
    • Selepe, M.A.1    Drewes, S.E.2    Van Heerden, F.R.3
  • 3
    • 77950924823 scopus 로고    scopus 로고
    • Total synthesis of hirtellanine a
    • Zheng, S.Y.; Shen, Z.W. Total synthesis of hirtellanine A. Tetrahedron Lett. 2010, 51, 2883-2887.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 2883-2887
    • Zheng, S.Y.1    Shen, Z.W.2
  • 4
    • 53749105472 scopus 로고    scopus 로고
    • Isoflavone glycosides: Synthesis and evaluation as α-glucosidase inhibitors
    • Wei, G.; Yu, B. Isoflavone glycosides: Synthesis and evaluation as α-glucosidase inhibitors. Eur. J. Org. Chem. 2008, 3156-3163.
    • (2008) Eur. J. Org. Chem. , pp. 3156-3163
    • Wei, G.1    Yu, B.2
  • 5
    • 71049127438 scopus 로고    scopus 로고
    • 7-hydroxy-benzopyran-4-one derivatives: A novel pharmacophore of peroxisome proliferator-activated receptor ? and -? (ppar? and ?) dual agonists
    • Matin, A.; Gavande, N.; Kim, M.S.; Yang, N.X.; Salam, N.K.; Hanrahan, J.R.; Roubin, R.H.; Hibbs, D.E. 7-Hydroxy-benzopyran-4-one derivatives: A novel pharmacophore of peroxisome proliferator-activated receptor ? and -? (PPAR? and ?) dual agonists. J. Med. Chem. 2009, 52, 6835-6850.
    • (2009) J. Med. Chem. , vol.52 , pp. 6835-6850
    • Matin, A.1    Gavande, N.2    Kim, M.S.3    Yang, N.X.4    Salam, N.K.5    Hanrahan, J.R.6    Roubin, R.H.7    Hibbs, D.E.8
  • 6
    • 77950028982 scopus 로고    scopus 로고
    • Total synthesis, antiprotozoal and cytotoxicity activities of rhuschalcone vi and analogs
    • Mihigo, S.O.; Mammo, W.; Bezabih, M.; Andrae-Marobela, K.; Abegaz, B.M. Total synthesis, antiprotozoal and cytotoxicity activities of rhuschalcone VI and analogs. Bioorg. Med. Chem. 2010, 18, 2464-2473.
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 2464-2473
    • Mihigo, S.O.1    Mammo, W.2    Bezabih, M.3    Andrae-Marobela, K.4    Abegaz, B.M.5
  • 11
    • 26844433863 scopus 로고    scopus 로고
    • Practical and efficient suzuki-miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by recyclable pd (0)/c
    • Felpin, F.-X. Practical and efficient Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by recyclable Pd(0)/C. J. Org. Chem. 2005, 70, 8575-8578.
    • (2005) J. Org. Chem. , vol.70 , pp. 8575-8578
    • Felpin, F.-X.1
  • 12
    • 33847260626 scopus 로고    scopus 로고
    • Practical and efficient entry to isoflavones by pd(0)/c-mediated suzuki-miyaura reaction. total synthesis of geranylated isoflavones
    • Felpin, F.-X.; Lory, C.; Sow, H.; Acherar, S. Practical and efficient entry to isoflavones by Pd(0)/C-mediated Suzuki-Miyaura reaction. Total synthesis of geranylated isoflavones. Tetrahedron 2007, 63, 3010-3016.
    • (2007) Tetrahedron , vol.63 , pp. 3010-3016
    • Felpin, F.-X.1    Lory, C.2    Sow, H.3    Acherar, S.4
  • 13
    • 84980108064 scopus 로고
    • Condensationen von ketonen mit aldehyden
    • Claisen, L.; Claparède, A. Condensationen von Ketonen mit Aldehyden. Chem. Ber. 1881, 14, 2460-2468.
    • (1881) Chem. Ber. , vol.14 , pp. 2460-2468
    • Claisen, L.1    Claparède, A.2
  • 15
    • 0033600699 scopus 로고    scopus 로고
    • Organolithium mediated synthesis of prenylchalcones as potential inhibitors of chemoresistance
    • Daskiewicz, J.B.; Comte, G.; Barron, D.; Di Pietro, A.; Thomasson, F. Organolithium mediated synthesis of prenylchalcones as potential inhibitors of chemoresistance. Tetrahedron Lett. 1999, 40, 7095-7098.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 7095-7098
    • Daskiewicz, J.B.1    Comte, G.2    Barron, D.3    Di Pietro, A.4    Thomasson, F.5
  • 17
    • 0141495522 scopus 로고    scopus 로고
    • Substituent effects in the bf3-mediated acylation of phenols with cinnamic acids
    • Daskiewicz, J.-B.; Barron, D. Substituent effects in the BF3-mediated acylation of phenols with cinnamic acids. Nat. Prod. Res. 2003, 17, 347-350.
    • (2003) Nat. Prod. Res. , vol.17 , pp. 347-350
    • Daskiewicz, J.-B.1    Barron, D.2
  • 19
    • 33846481141 scopus 로고    scopus 로고
    • Sequential coupling-isomerization-coupling reactions - A novel three-component synthesis of aryl chalcones
    • Liao, W.-W.; Mueller, T.J. J. Sequential coupling-isomerization-coupling reactions - A novel three-component synthesis of aryl chalcones. Synlett 2006, 3469-3473.
    • (2006) Synlett , pp. 3469-3473
    • Liao, W.-W.1    Mueller, T.J.J.2
  • 20
    • 33845456747 scopus 로고    scopus 로고
    • Coupling-isomerization synthesis of chalcones
    • Braun, R.U.; Ansorge, M.; Mueller, T.J.J. Coupling-isomerization synthesis of chalcones. Chem. Eur. J. 2006, 12, 9081-9094.
    • (2006) Chem. Eur. J. , vol.12 , pp. 9081-9094
    • Braun, R.U.1    Ansorge, M.2    Mueller, T.J.J.3
  • 21
    • 0038684441 scopus 로고    scopus 로고
    • An efficient synthesis of chalcones based on the suzuki reaction
    • Eddarir, S.; Cotelle, N.; Bakkour, Y.; Rolando, C. An efficient synthesis of chalcones based on the Suzuki reaction. Tetrahedron Lett. 2003, 44, 5359-5363.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 5359-5363
    • Eddarir, S.1    Cotelle, N.2    Bakkour, Y.3    Rolando, C.4
  • 22
    • 0033574716 scopus 로고    scopus 로고
    • A new method for the synthesis of ketones: The palladium-catalyzed cross-coupling of acid chlorides with arylboronic acids
    • Haddach, M.; McCarthy, J.R. A new method for the synthesis of ketones: The palladium-catalyzed cross-coupling of acid chlorides with arylboronic acids. Tetrahedron Lett. 1999, 40, 3109-3112.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 3109-3112
    • Haddach, M.1    McCarthy, J.R.2
  • 23
    • 79251595233 scopus 로고    scopus 로고
    • Palladium-catalyzed direct cross-coupling of potassium styryltrifluoroborates and benzoyl chlorides - A one step method for chalcone synthesis
    • Al-Masum, M.; Ng, E.; Wai, M.C. Palladium-catalyzed direct cross-coupling of potassium styryltrifluoroborates and benzoyl chlorides - a one step method for chalcone synthesis. Tetrahedron Lett. 2011, 52, 1008-1010.
    • (2011) Tetrahedron Lett. , vol.52 , pp. 1008-1010
    • Al-Masum, M.1    Ng, E.2    Wai, M.C.3
  • 24
    • 49949106824 scopus 로고    scopus 로고
    • Synthesis of aryl ketones by cross-coupling reaction of arylboronic acids with carboxylic anhydrides in aqueous phase
    • Xin, B.-W. Synthesis of aryl ketones by cross-coupling reaction of arylboronic acids with carboxylic anhydrides in aqueous phase. Synth. Commun. 2008, 38, 2826-2837.
    • (2008) Synth. Commun. , vol.38 , pp. 2826-2837
    • Xin, B.-W.1
  • 25
    • 84862823142 scopus 로고    scopus 로고
    • Synthesis and cytotoxicity evaluation of biaryl-based chalcones and their potential in tnf alpha-induced nuclear factor-kappa b activation inhibition
    • Zuo, Y.; Yu, Y.; Wang, S.; Shao, W.; Zhou, B.; Lin, L.; Luo, Z.; Huang, R.; Du, J.; Bu, X. Synthesis and cytotoxicity evaluation of biaryl-based chalcones and their potential in TNF alpha-induced nuclear factor-kappa B activation inhibition. Eur. J. Med. Chem. 2012, 50, 393-404.
    • (2012) Eur. J. Med. Chem. , vol.50 , pp. 393-404
    • Zuo, Y.1    Yu, Y.2    Wang, S.3    Shao, W.4    Zhou, B.5    Lin, L.6    Luo, Z.7    Huang, R.8    Du, J.9    Bu, X.10
  • 26
    • 84860221082 scopus 로고    scopus 로고
    • Green synthesis of novel chalcone and coumarin derivatives via suzuki coupling reaction
    • Vieira, L.C.C.; Paixão, M.W.; Corrêa, A.G. Green synthesis of novel chalcone and coumarin derivatives via Suzuki coupling reaction. Tetrahedron Lett. 2012, 53, 2715-2718.
    • (2012) Tetrahedron Lett. , vol.53 , pp. 2715-2718
    • Vieira, L.C.C.1    Paixão, M.W.2    Corrêa, A.G.3
  • 27
    • 33748899925 scopus 로고
    • 322. molecular rearrangement of some o-acyloxyacetophenones and the mechanism of the production of 3-acylchromones
    • Baker, W. 322. Molecular rearrangement of some o-acyloxyacetophenones and the mechanism of the production of 3-acylchromones. J. Chem. Soc. 1933, 1381-1389.
    • (1933) J. Chem. Soc. , pp. 1381-1389
    • Baker, W.1
  • 28
    • 0242435492 scopus 로고
    • 387. synthetical experiments in the chromone group. part xiv. The action of sodamide on 1-acyloxy-2-acetonaphthones
    • Mahal, H.S.; Venkataraman, K. 387. Synthetical experiments in the chromone group. Part XIV. The action of sodamide on 1-acyloxy-2-acetonaphthones. J. Chem. Soc. 1934, 1767-1769.
    • (1934) J. Chem. Soc. , pp. 1767-1769
    • Mahal, H.S.1    Venkataraman, K.2
  • 29
    • 77951759514 scopus 로고    scopus 로고
    • Solid phase baker-venkataraman rearrangement under solvent-free condition using grinding technique
    • Sharma, D.; Kumar, S.; Makrandi, J.K. Solid phase Baker-Venkataraman rearrangement under solvent-free condition using grinding technique. Green Chem. Lett. Rev. 2009, 2, 53-55.
    • (2009) Green Chem. Lett. Rev. , vol.2 , pp. 53-55
    • Sharma, D.1    Kumar, S.2    Makrandi, J.K.3
  • 31
    • 0029931889 scopus 로고    scopus 로고
    • Aspects of the algar-flynn-oyamada (afo) reaction
    • Bennett, M.; Burke, A.J.; O'Sullivan, W.I. Aspects of the Algar-Flynn-Oyamada (AFO) reaction. Tetrahedron 1996, 52, 7163-7178.
    • (1996) Tetrahedron , vol.52 , pp. 7163-7178
    • Bennett, M.1    Burke, A.J.2    O'Sullivan, W.I.3
  • 32
    • 0035842121 scopus 로고    scopus 로고
    • An environmentally benign synthesis of aurones and flavones from 2'-acetoxychalcones using n-tetrabutylammonium tribromide
    • Bose, G.; Mondal, E.; Khan, A.T.; Bordoloi, M.J. An environmentally benign synthesis of aurones and flavones from 2'-acetoxychalcones using n-tetrabutylammonium tribromide. Tetrahedron Lett. 2001, 42, 8907-8909.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 8907-8909
    • Bose, G.1    Mondal, E.2    Khan, A.T.3    Bordoloi, M.J.4
  • 33
    • 78449302625 scopus 로고    scopus 로고
    • Divergent approach to flavones and aurones via dihaloacrylic acids unexpected dependence on the halogen atom
    • Kraus, G.A.; Gupta, V. Divergent approach to flavones and aurones via dihaloacrylic acids. Unexpected dependence on the halogen atom. Org. Lett. 2010, 12, 5278-5280.
    • (2010) Org. Lett. , vol.12 , pp. 5278-5280
    • Kraus, G.A.1    Gupta, V.2
  • 34
    • 33750452718 scopus 로고    scopus 로고
    • Synthesis of 2,3,6,8-tetrasubstituted chromone scaffolds
    • Dahlen, K.; Wallen, E.A.A.; Grotli, M.; Luthman, K. Synthesis of 2,3,6,8-tetrasubstituted chromone scaffolds. J. Org. Chem. 2006, 71, 6863-6871.
    • (2006) J Org Chem , vol.71 , pp. 6863-6871
    • Dahlen, K.1    Wallen, E.A.A.2    Grotli, M.3    Luthman, K.4
  • 35
    • 57349148119 scopus 로고    scopus 로고
    • Efficient synthesis of chromone and flavonoid derivatives with diverse heterocyclic units
    • Arai, M.A.; Sato, M.; Sawada, K.; Hosoya, T.; Ishibashi, M. Efficient synthesis of chromone and flavonoid derivatives with diverse heterocyclic units. Chem.-Asian J. 2008, 3, 2056-2064.
    • (2008) Chem.-Asian J. , vol.3 , pp. 2056-2064
    • Arai, M.A.1    Sato, M.2    Sawada, K.3    Hosoya, T.4    Ishibashi, M.5
  • 36
    • 67651102760 scopus 로고    scopus 로고
    • Synthesis of a range of polyhydroxy 8-aryl flavones
    • Larsen, L.; Yoon, D.H.; Weavers, R.T. Synthesis of a range of polyhydroxy 8-aryl flavones. Synth. Commun. 2009, 39, 2935-2948.
    • (2009) Synth. Commun. , vol.39 , pp. 2935-2948
    • Larsen, L.1    Yoon, D.H.2    Weavers, R.T.3
  • 37
    • 77955682061 scopus 로고    scopus 로고
    • Synthesis of some new biheterocycles by a one-pot suzuki-miyaura coupling reaction
    • Deodhar, M.; Black, D.S.; Chan, D.S.-H.; Kumar, N. Synthesis of some new biheterocycles by a one-pot Suzuki-Miyaura coupling reaction. Heterocycles 2010, 80, 1267-1274.
    • (2010) Heterocycles , vol.80 , pp. 1267-1274
    • Deodhar, M.1    Black, D.S.2    Chan, D.S.-H.3    Kumar, N.4
  • 38
    • 77956471409 scopus 로고    scopus 로고
    • Synthesis of 7,8-diarylflavones by site-selective suzuki-miyaura reactions
    • Malik, I.; Hussain, M.; Hung, N.T.; Villinger, A.; Langer, P. Synthesis of 7,8-diarylflavones by site-selective Suzuki-Miyaura reactions. Synlett 2010, 2244-2246.
    • (2010) Synlett , pp. 2244-2246
    • Malik, I.1    Hussain, M.2    Hung, N.T.3    Villinger, A.4    Langer, P.5
  • 39
    • 80052918619 scopus 로고    scopus 로고
    • A chrysin analog exhibited strong inhibitory activities against both pge(2) and no production
    • Che, H.; Lim, H.; Kim, H.P.; Park, H. A chrysin analog exhibited strong inhibitory activities against both PGE(2) and NO production. Eur. J. Med. Chem. 2011, 46, 4657-4660.
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 4657-4660
    • Che, H.1    Lim, H.2    Kim, H.P.3    Park, H.4
  • 40
    • 84876771865 scopus 로고    scopus 로고
    • Facile synthesis of new substituted 3-aryl/heteroarylflavones by suzuki-miyaura coupling of 3-bromoflavone with substituted aryl/ heteroarylboronic acids
    • Joshi, V.; Hatim, J.G. Facile synthesis of new substituted 3-aryl/heteroarylflavones by Suzuki-Miyaura coupling of 3-bromoflavone with substituted aryl/heteroarylboronic acids. Indian J. Heterocycl. Chem. 2011, 21, 111-116.
    • (2011) Indian J. Heterocycl. Chem. , vol.21 , pp. 111-116
    • Joshi, V.1    Hatim, J.G.2
  • 41
    • 84857805263 scopus 로고    scopus 로고
    • Efficient synthesis of arylated flavones by site-selective suzuki-miyaura cross-coupling ceactions of the cis(triflate) of 57- and 7,8-dihydroxyflavone
    • Eleya, N.; Malik, I.; Reimann, S.; Wittler, K.; Hein, M.; Patonay, T.; Villinger, A.; Ludwig, R.; Langer, P. Efficient synthesis of arylated flavones by site-selective Suzuki-Miyaura cross-coupling ceactions of the cis(triflate) of 5,7- and 7,8-dihydroxyflavone. Eur. J. Org. Chem. 2012, 2012, 1639-1652.
    • (2012) Eur. J. Org. Chem. , vol.2012 , pp. 1639-1652
    • Eleya, N.1    Malik, I.2    Reimann, S.3    Wittler, K.4    Hein, M.5    Patonay, T.6    Villinger, A.7    Ludwig, R.8    Langer, P.9
  • 43
  • 44
    • 0025735743 scopus 로고
    • A new strategy for the synthesis of biflavonoids via arylboronic acids
    • Muller, D.; Fleury, J.P. A new strategy for the synthesis of biflavonoids via arylboronic acids. Tetrahedron Lett. 1991, 32, 2229-2232.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 2229-2232
    • Muller, D.1    Fleury, J.P.2
  • 45
    • 0032509259 scopus 로고    scopus 로고
    • Total synthesis of robustaflavone, a potential anti-hepatitis b agent
    • Zembower, D.E.; Zhang, H.P. Total synthesis of robustaflavone, a potential anti-hepatitis B agent. J. Org. Chem. 1998, 63, 9300-9305.
    • (1998) J. Org. Chem. , vol.63 , pp. 9300-9305
    • Zembower, D.E.1    Zhang, H.P.2
  • 46
    • 4644251731 scopus 로고    scopus 로고
    • Synthesis of gem-difluoromethylenated biflavonoid via the suzuki coupling reaction
    • Zheng, X.; Meng, W.D.; Qing, F.L. Synthesis of gem-difluoromethylenated biflavonoid via the Suzuki coupling reaction. Tetrahedron Lett. 2004, 45, 8083-8085.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 8083-8085
    • Zheng, X.1    Meng, W.D.2    Qing, F.L.3
  • 47
    • 0003096846 scopus 로고
    • The isoflavonoids
    • Geissman, T.A., Ed.; Pergamon Press Inc.: Oxford, UK
    • Ollis, W.D. The Isoflavonoids. In The Chemistry of Flavonoids; Geissman, T.A., Ed.; Pergamon Press Inc.: Oxford, UK, 1962; pp. 353-440.
    • (1962) The Chemistry of Flavonoids , pp. 353-440
    • Ollis, W.D.1
  • 49
    • 85052880568 scopus 로고
    • Isoflavonoids
    • Harborne, J.B., Ed.; Chapman and Hall: London, UK
    • Dewick, P.M. Isoflavonoids. In The Flavonoids: Advances in Research since 1986; Harborne, J.B., Ed.; Chapman and Hall: London, UK, 1994; pp. 117-238.
    • (1994) The Flavonoids: Advances in Research since 1986 , pp. 117-238
    • Dewick, P.M.1
  • 51
    • 60249097849 scopus 로고    scopus 로고
    • A wacker-cook synthesis of isoflavones: Formononetine
    • Granados-Covarrubias, E.H.; Maldonado, L.A. A Wacker-Cook synthesis of isoflavones: formononetine. Tetrahedron Lett. 2009, 50, 1542-1545.
    • (2009) Tetrahedron Lett. , vol.50 , pp. 1542-1545
    • Granados-Covarrubias, E.H.1    Maldonado, L.A.2
  • 52
    • 79960615517 scopus 로고    scopus 로고
    • A novel synthesis of isoflavones via copper(i)-catalyzed intramolecular cyclization reaction
    • Li, Q.-L.; Liu, Q.-L.; Ge, Z.-Y.; Zhu, Y.-M. A novel synthesis of isoflavones via copper(I)-catalyzed intramolecular cyclization reaction. Helv. Chim. Acta 2011, 94, 1304-1309.
    • (2011) Helv. Chim. Acta , vol.94 , pp. 1304-1309
    • Li, Q.-L.1    Liu, Q.-L.2    Ge, Z.-Y.3    Zhu, Y.-M.4
  • 53
    • 76949099394 scopus 로고
    • Novel synthesis of isoflavones by the palladium-catalyzed cross-coupling reaction of 3-bromochromones with arylboronic acids or their esters
    • Hoshino, Y.; Miyaura, N.; Suzuki, A. Novel synthesis of isoflavones by the palladium-catalyzed cross-coupling reaction of 3-bromochromones with arylboronic acids or their esters. Bull. Chem. Soc. Jpn. 1988, 61, 3008-3010.
    • (1988) Bull. Chem. Soc. Jpn. , vol.61 , pp. 3008-3010
    • Hoshino, Y.1    Miyaura, N.2    Suzuki, A.3
  • 54
    • 34547777869 scopus 로고    scopus 로고
    • Microwave-assisted suzuki-miyaura and heck-mizoroki cross-coupling reactions of aryl chlorides and bromides in water using stable benzothiazole-based palladium(ii) precatalysts
    • Dawood, K.M. Microwave-assisted Suzuki-Miyaura and Heck-Mizoroki cross-coupling reactions of aryl chlorides and bromides in water using stable benzothiazole-based palladium(II) precatalysts. Tetrahedron 2007, 63, 9642-9651.
    • (2007) Tetrahedron , vol.63 , pp. 9642-9651
    • Dawood . K, M.1
  • 55
    • 33644984253 scopus 로고    scopus 로고
    • Oxazoline chemistry. part 11: Syntheses of natural and synthetic isoflavones, stilbenes and related species via c-c bond formation promoted by a pd-oxazoline complex
    • Eisnor, C.R.; Gossage, R.A.; Yadav, P.N. Oxazoline Chemistry. Part 11: Syntheses of natural and synthetic isoflavones, stilbenes and related species via C-C bond formation promoted by a Pd-oxazoline complex. Tetrahedron 2006, 62, 3395-3401.
    • (2006) Tetrahedron , vol.62 , pp. 3395-3401
    • Eisnor, C.R.1    Gossage, R.A.2    Yadav, P.N.3
  • 56
    • 17844363987 scopus 로고    scopus 로고
    • Efficient synthesis of isoflavone analogues via a suzuki coupling reaction
    • Ding, K.; Wang, S.M. Efficient synthesis of isoflavone analogues via a Suzuki coupling reaction. Tetrahedron Lett. 2005, 46, 3707-3709.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 3707-3709
    • Ding, K.1    Wang, S.M.2
  • 57
    • 77955413543 scopus 로고    scopus 로고
    • An efficient synthesis of daidzein, dimethyldaidzein, and isoformononetin
    • Biegasiewicz, K.F.; St Denis, J.D.; Carroll, V.M.; Priefer, R. An efficient synthesis of daidzein, dimethyldaidzein, and isoformononetin. Tetrahedron Lett. 2010, 51, 4408-4410.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 4408-4410
    • Biegasiewicz, K.F.1    St Denis, J.D.2    Carroll, V.M.3    Priefer, R.4
  • 58
    • 70449367182 scopus 로고
    • A new and efficient synthesis of 3-halogenated 4h-1-benzopyran-4-ones
    • Gammill, B.R. A new and efficient synthesis of 3-halogenated 4H-1-benzopyran-4-ones. Synthesis 1979, 901-903.
    • (1979) Synthesis , pp. 901-903
    • Gammill, B.R.1
  • 59
    • 77957834673 scopus 로고    scopus 로고
    • Palladium-catalyzed oxidative cross-coupling reaction of arylboronic acids with diazoesters for stereoselective synthesis of (e)-ćα- diarylacrylates
    • Tsoi, Y.-T.; Zhou, Z.; Chan, A.S.C.; Yu, W.-Y. Palladium-catalyzed oxidative cross-coupling reaction of arylboronic acids with diazoesters for stereoselective synthesis of (E)-ćα-diarylacrylates. Org. Lett. 2010, 12, 4506-4509.
    • (2010) Org. Lett. , vol.12 , pp. 4506-4509
    • Tsoi, Y.-T.1    Zhou, Z.2    Chan, A.S.C.3    Yu, W.-Y.4
  • 60
    • 77956179682 scopus 로고    scopus 로고
    • Structure-activity relationship study of glaziovianin a against cell cycle progression and spindle formation of hela s3 cells
    • Ikedo, A.; Hayakawa, I.; Usui, T.; Kazami, S.; Osada, H.; Kigoshi, H. Structure-activity relationship study of glaziovianin A against cell cycle progression and spindle formation of HeLa S3 cells. Bioorg. Med. Chem. Lett. 2010, 20, 5402-5404.
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 5402-5404
    • Ikedo, A.1    Hayakawa, I.2    Usui, T.3    Kazami, S.4    Osada, H.5    Kigoshi, H.6
  • 61
    • 33745642100 scopus 로고    scopus 로고
    • Structural studies on bioactive compounds. synthesis and biological properties of fluoro-, methoxyl-, and amino-substituted 3-phenyl-4h-1- benzopyran-4-ones and a comparison of their antitumor activities with the activities of related 2-phenylbenzothiazoles
    • Vasselin, D.A.; Westwell, A.D.; Matthews, C.S.; Bradshaw, T.D.; Stevens, M.F.G. Structural studies on bioactive compounds. Synthesis and biological properties of fluoro-, methoxyl-, and amino-substituted 3-phenyl-4H-1- benzopyran-4-ones and a comparison of their antitumor activities with the activities of related 2-phenylbenzothiazoles. J. Med. Chem. 2006, 49, 3973-3981.
    • (2006) J. Med. Chem. , vol.49 , pp. 3973-3981
    • Vasselin, D.A.1    Westwell, A.D.2    Matthews, C.S.3    Bradshaw, T.D.4    Stevens, M.F.G.5
  • 62
    • 36849069399 scopus 로고    scopus 로고
    • Synthesis of glaziovianin a: A potent antitumor isoflavone
    • Hayakawa, I.; Ikedo, A.; Kigoshi, H. Synthesis of glaziovianin A: A potent antitumor isoflavone. Chem. Lett. 2007, 36, 1382-1383.
    • (2007) Chem. Lett. , vol.36 , pp. 1382-1383
    • Hayakawa, I.1    Ikedo, A.2    Kigoshi, H.3
  • 63
  • 67
    • 84920087946 scopus 로고    scopus 로고
    • Flavonoids as nutraceuticals
    • Grotewold, E., Ed; Springer Science and Business media: New York, NY, USA
    • Lin, J.-K.; Weng, M.-S. Flavonoids as Nutraceuticals. In The Science of Flavonoids; Grotewold, E., Ed; Springer Science and Business media: New York, NY, USA, 2006.
    • (2006) The Science of Flavonoids
    • Lin, J.-K.1    Weng, M.-S.2
  • 68
    • 45949124293 scopus 로고
    • Synthesis of alpinum isoflavone, derrone and related pyranoisoflavones
    • Rao, K.S.R.M.; Iyer, C.S.R.; Iyer, P.R. Synthesis of alpinum isoflavone, derrone and related pyranoisoflavones. Tetrahedron 1987, 43, 3015-3019.
    • (1987) Tetrahedron , vol.43 , pp. 3015-3019
    • Rao, K.S.R.M.1    Iyer, C.S.R.2    Iyer, P.R.3
  • 69
    • 26844506653 scopus 로고
    • Synthesis of derrubone and robustone
    • Jain, A.C.; Jain, S.M. Synthesis of derrubone and robustone. Tetrahedron 1972, 28, 5063-5067.
    • (1972) Tetrahedron , vol.28 , pp. 5063-5067
    • Jain, A.C.1    Jain, S.M.2
  • 70
    • 40949091876 scopus 로고    scopus 로고
    • Synthesis and evaluation of derrubone and select analogues
    • Hastings, J.M.; Hadden, M.K.; Blagg, B.S.J. Synthesis and evaluation of derrubone and select analogues. J. Org. Chem. 2007, 73, 369-373.
    • (2007) J. Org. Chem. , vol.73 , pp. 369-373
    • Hastings, J.M.1    Hadden, M.K.2    Blagg, B.S.J.3
  • 71
    • 70450221333 scopus 로고    scopus 로고
    • Prenylated isoflavonoids: Botanical distribution, structures, biological activities and biotechnological studies. an update (1995-2006)
    • Botta, B.; Menendez, P.; Zappia, G.; de Lima, R.A.; Torge, R.; Delle Monache, G. Prenylated isoflavonoids: Botanical distribution, Structures, Biological activities and biotechnological studies. An update (1995-2006). Curr. Med. Chem. 2009, 16, 3414-3468.
    • (2009) Curr. Med. Chem. , vol.16 , pp. 3414-3468
    • Botta, B.1    Menendez, P.2    Zappia, G.3    De Lima, R.A.4    Torge, R.5    Delle Monache, G.6
  • 72
    • 80053602356 scopus 로고    scopus 로고
    • Total synthesis of the pyranocoumaronochromone lupinalbin h
    • Selepe, M.A.; Drewes, S.E.; van Heerden, F.R. Total synthesis of the pyranocoumaronochromone lupinalbin H. Tetrahedron 2011, 67, 8654-8658.
    • (2011) Tetrahedron , vol.67 , pp. 8654-8658
    • Selepe, M.A.1    Drewes, S.E.2    Van Heerden, F.R.3
  • 73
    • 33947645972 scopus 로고    scopus 로고
    • Isoflavonoids of the leguminosae
    • Veitch, N.C. Isoflavonoids of the Leguminosae. Nat. Prod. Rep. 2007, 24, 417-464.
    • (2007) Nat. Prod. Rep. , vol.24 , pp. 417-464
    • Veitch, N.C.1
  • 74
    • 67651071732 scopus 로고    scopus 로고
    • Isoflavonoids of the leguminosae
    • Veitch, N.C. Isoflavonoids of the Leguminosae. Nat. Prod. Rep. 2009, 26, 776-802.
    • (2009) Nat. Prod. Rep. , vol.26 , pp. 776-802
    • Veitch, N.C.1
  • 75
    • 66349116679 scopus 로고    scopus 로고
    • Hirtellanines a and b, a pair of isomeric isoflavonoid derivatives from campylotropis hirtella and their immunosuppressive activities
    • Shou, Q.Y.; Tan, Q.; Shen, Z.W. Hirtellanines A and B, a pair of isomeric isoflavonoid derivatives from Campylotropis hirtella and their immunosuppressive activities. Bioorg. Med. Chem. Lett. 2009, 19, 3389-3391.
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 3389-3391
    • Shou, Q.Y.1    Tan, Q.2    Shen, Z.W.3
  • 76
    • 0000662184 scopus 로고
    • Influence of structure on the rate of thermal rearrangement of aryl propargyl ethers to the chromenes gem-dimethyl effect
    • Harfenist, M.; Thom, E. Influence of structure on the rate of thermal rearrangement of aryl propargyl ethers to the chromenes. Gem-dimethyl effect. J. Org. Chem. 1972, 37, 841-848.
    • (1972) J. Org. Chem. , vol.37 , pp. 841-848
    • Harfenist, M.1    Thom, E.2
  • 77
    • 24644445060 scopus 로고    scopus 로고
    • Neoflavones. 2. methods for synthesizing and modifying 4-arylcoumarins
    • Garazd, M.M.; Garazd, Y.L.; Khilya, V.P. Neoflavones. 2. Methods for synthesizing and modifying 4-arylcoumarins. Chem. Nat. Comp. 2005, 41, 245-271.
    • (2005) Chem. Nat. Comp. , vol.41 , pp. 245-271
    • Garazd, M.M.1    Garazd, Y.L.2    Khilya, V.P.3
  • 78
    • 69249123855 scopus 로고    scopus 로고
    • Nickel-catalysed negishi cross-coupling reactions: Scope and mechanisms
    • Phapale, V.B.; Cardenas, D.J. Nickel-catalysed Negishi cross-coupling reactions: scope and mechanisms. Chem. Soc. Rev. 2009, 38, 1598-1607.
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 1598-1607
    • Phapale, V.B.1    Cardenas, D.J.2
  • 79
    • 34548774475 scopus 로고    scopus 로고
    • General and efficient route for the synthesis of 3,4-disubstituted coumarins via pd-catalyzed site-selective cross-coupling reactions
    • Zhang, L.; Meng, T.; Fan, R.; Wu, H. General and efficient route for the synthesis of 3,4-disubstituted coumarins via Pd-catalyzed site-selective cross-coupling reactions. J. Org. Chem. 2007, 72, 7279-7286.
    • (2007) J. Org. Chem. , vol.72 , pp. 7279-7286
    • Zhang, L.1    Meng, T.2    Fan, R.3    Wu, H.4
  • 80
    • 84861526875 scopus 로고    scopus 로고
    • Chemoselective suzuki-miyaura reactions of 4-trifluoromethylsulfonyloxy- 6-bromocoumarin
    • Akrawi, O.A.; Nagy, G.Z.; Patonay, T.; Villinger, A.; Langer, P. Chemoselective Suzuki-Miyaura reactions of 4-trifluoromethylsulfonyloxy-6- bromocoumarin. Tetrahedron Lett. 2012, 53, 3206-3209.
    • (2012) Tetrahedron Lett. , vol.53 , pp. 3206-3209
    • Akrawi, O.A.1    Nagy, G.Z.2    Patonay, T.3    Villinger, A.4    Langer, P.5
  • 81
    • 84857565585 scopus 로고    scopus 로고
    • A facile route to flavone and neoflavone backbones via a regioselective palladium catalyzed oxidative heck reaction
    • Khoobi, M.; Alipour, M.; Zarei, S.; Jafarpour, F.; Shafiee, A. A facile route to flavone and neoflavone backbones via a regioselective palladium catalyzed oxidative Heck reaction. J. Chem. Soc., Chem. Commun. 2012, 48, 2985-2987.
    • (2012) J. Chem. Soc., Chem. Commun. , vol.48 , pp. 2985-2987
    • Khoobi, M.1    Alipour, M.2    Zarei, S.3    Jafarpour, F.4    Shafiee, A.5
  • 82
    • 84863179519 scopus 로고    scopus 로고
    • Palladium-catalyzed oxidative heck coupling reaction for direct synthesis of 4-arylcoumarins using coumarins and arylboronic acids
    • Li, Y.; Qi, Z.; Wang, H.; Fu, X.; Duan, C. Palladium-catalyzed oxidative Heck coupling reaction for direct synthesis of 4-arylcoumarins using coumarins and arylboronic acids. J. Org. Chem. 2012, 77, 2053-2057.
    • (2012) J. Org. Chem. , vol.77 , pp. 2053-2057
    • Li, Y.1    Qi, Z.2    Wang, H.3    Fu, X.4    Duan, C.5
  • 84
    • 0033035130 scopus 로고    scopus 로고
    • Synthesis of c-ring hydroxylated neoflavonoids by ligand coupling reactions
    • Donnelly, D.M.X.; Finet, J.P.; Guiry, P.J.; Rea, M.D. Synthesis of C-ring hydroxylated neoflavonoids by ligand coupling reactions. Synth. Commun. 1999, 29, 2719-2730.
    • (1999) Synth. Commun. , vol.29 , pp. 2719-2730
    • Donnelly, D.M.X.1    Finet, J.P.2    Guiry, P.J.3    Rea, M.D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.