Efficient synthesis of 2-benzofuranyl C-glycosides by one-pot cascade reaction of sugar alkynes and substituted 2-iodophenols

References

• Hansen, M. R.; Hurley, L. H. Pluramycins. Old drugs having modern friends in structural biology. Acc. Chem. Res. 1996, 29(5), 249–258. DOI: 10.1021/ar950167a.
   Web of Science ®Google Scholar
• Bililign, T.; Griffith, B. R.; Thorson, J. S. Structure, activity, synthesis and biosynthesis of aryl-C-glycosides. Nat. Prod. Rep. 2005, 22(6), 742–760. DOI: 10.1039/b407364a.
   PubMed Web of Science ®Google Scholar
• Matsuda, S.; Fillo, J. D.; Henry, A. A.; Rai, P.; Wilkens, S. J.; Dwyer, T. J.; Geierstanger, B. H.; Wemmer, D. E.; Schultz, P. G.; Spraggon, G.; Romesberg, F. E. Efforts toward expansion of the genetic alphabet: structure and replication of unnatural base pairs. J. Am. Chem. Soc. 2007, 129(34), 10466–10473. DOI: 10.1021/ja072276d.
   PubMed Web of Science ®Google Scholar
• Leconte, A. M.; Wang, G. T.; Matsuda, S.; Capek, P.; Hari, Y.; Romesberg, F. E. Discovery, characterization, and optimization of an unnatural base pair for expansion of the genetic alphabet. J. Am. Chem. Soc. 2008, 130(7), 2336–2343. DOI: 10.1021/ja078223d.
   PubMed Web of Science ®Google Scholar
• Hari, Y.; Hwang, G. T.; Leconte, A. M.; Joubert, N.; Hocek, M.; Romesberg, F. E. Optimization of the pyridyl nucleobase scaffold for polymerase recognition and unnatural base pair replication. Chembiochem. 2008, 9(17), 2796–2799. DOI: 10.1002/cbic.200800577.
   PubMed Web of Science ®Google Scholar
• Štambaský, J.; Hocek, M.; Kočovský, P. C-nucleosides: synthetic strategies and biological applications. Chem. Rev. 2009, 109(12), 6729–6764. DOI: 10.1021/cr9002165.
   PubMed Web of Science ®Google Scholar
• Necas, D.; Hidasova, D.; Hocek, M.; Kotora, M. Modular synthesis of 1-α- and 1-β-(indol-2-yl)-2'-deoxyribose C-nucleosides. Org. Biomol. Chem. 2011, 9(17), 5934–5937. DOI: 10.1039/c1ob05844d.
   PubMed Web of Science ®Google Scholar
• Balachari, D.; O'Doherty, G. A. Sharpless asymmetric dihydroxylation of 5-aryl-2-vinylfurans: application to the synthesis of the spiroketal moiety of papulacandin D. Org. Lett. 2000, 2(6), 863–866. DOI: 10.1021/ol0000253.
   PubMed Web of Science ®Google Scholar
• Kaelin, D. E.; Jr.; Sparks, S. M.; Plake, H. R.; Martin, S. F. Regioselective synthesis of unsymmetrical C-aryl glycosides using silicon tethers as disposable linkers. J. Am. Chem. Soc. 2003, 125(43), 12994–12995. DOI: 10.1021/ja0375582.
   PubMed Web of Science ®Google Scholar
• Liu, T.; Kharel, M. K.; Zhu, L.; Bright, S. A.; Mattingly, C.; Adams, V. R.; Rohr, J. Inactivation of the ketoreductase gilU gene of the gilvocarcin biosynthetic gene cluster yields new analogues with partly improved biological activity. Chembiochem. 2009, 10(2), 278–286. DOI: 10.1002/cbic.200800348.
   PubMed Web of Science ®Google Scholar
• Carlsson, B.; Singh, B. N.; Temciuc, M.; Nilsson, S.; Li, Y. L.; Mellin, C.; Malm, J. Synthesis and preliminary characterization of a novel antiarrhythmic compound (KB130015) with an improved toxicity profile compared with amiodarone. J. Med. Chem. 2002, 45(3), 623–630. DOI: 10.1021/jm001126.
   PubMed Web of Science ®Google Scholar
• Flynn, B. L.; Hamel, E.; Jung, M. K. One-pot synthesis of benzo[b]furan and indole inhibitors of tubulin polymerization. J. Med. Chem. 2002, 45(12), 2670–2673. DOI: 10.1021/jm020077t.
   PubMed Web of Science ®Google Scholar
• Ando, K.; Kawamura, Y.; Akai, Y.; Kunitomo, J. I.; Yokomizo, T.; Yamashita, M.; Ohta, S.; Ohishi, T.; Ohishi, Y. Preparation of 2-, 3-, 4- and 7-(2-alkylcarbamoyl-1-alkylvinyl)benzo[b]furans and their BLT1 and/or BLT2 inhibitory activities. Org. Biomol. Chem. 2008, 6(2), 296–307. DOI: 10.1039/b710935k.
   PubMed Web of Science ®Google Scholar
• Yeung, K. S.; Peng, X. S.; Wu, J.; Fan, R.; Hou, X. L. Chapter 4.3 – five-membered ring systems: furans and benzofurans. Prog. Heterocycl. Chem. 2013, 23, 183. DOI: 10.1016/B978-0-08-099406-2.00008-X.
   Google Scholar
• Takasaki, M.; Konoshima, T.; Komatsu, K.; Tokuda, H.; Nishino, H. Anti-tumor-promoting activity of lignans from the aerial part of Saussurea medusa. Cancer Lett. 2000, 158(1), 53–59. DOI: 10.1016/s0304-3835(00)00499-7.
   PubMed Web of Science ®Google Scholar
• Lambert, J. D.; Meyers, R. O.; Timmermann, B. N.; Dorr, R. T. tetra-O-methylnordihydroguaiaretic acid inhibits melanoma in vivo. Cancer Lett. 2001, 171(1), 47–56. DOI: 10.1016/s0304-3835(01)00560-2.
   PubMed Web of Science ®Google Scholar
• Hranjec, M.; Sovic, I.; Ratkaj, I.; Pavlovic, G.; Ilic, N.; Valjalo, L.; Pavelic, K.; Pavelic, S. K.; Zamola, G. K. Antiproliferative potency of novel benzofuran-2-carboxamides on tumour cell lines: cell death mechanisms and determination of crystal structure. Eur. J. Med. Chem. 2013, 59, 111–119. DOI: 10.1016/j.ejmech.2012.11.009.
   PubMed Web of Science ®Google Scholar
• Bazin, M. A.; Bodero, L.; Tomasoni, C.; Rousseau, B.; Roussakis, C.; Marchand, P. Synthesis and antiproliferative activity of benzofuran-based analogs of cercosporamide against non-small cell lung cancer cell lines. Eur. J. Med. Chem. 2013, 69, 823–832. DOI: 10.1016/j.ejmech.2013.09.013.
   PubMed Web of Science ®Google Scholar
• Xie, F.; Zhu, H.; Zhang, H.; Lang, Q.; Tang, L.; Huang, Q.; Yu, L. In vitro and in vivo characterization of a benzofuran derivative, a potential anticancer agent, as a novel Aurora B kinase inhibitor. Eur. J. Med. Chem. 2015, 89, 310–319. DOI: 10.1016/j.ejmech.2014.10.044.
   PubMed Web of Science ®Google Scholar
• Craigo, J.; Callahan, M.; Huang, R. C. C.; DeLucia, A. L. Inhibition of human papillomavirus type 16 gene expression by nordihydroguaiaretic acid plant lignan derivatives. Antiviral Res. 2000, 47(1), 19–28. DOI: 10.1016/s0166-3542(00)00089-9.
   PubMed Web of Science ®Google Scholar
• Galal, S. A.; El-All, A. S. A.; Abdallah, M. M.; El-Diwani, H. I. Synthesis of potent antitumor and antiviral benzofuran derivatives. Bioorg. Med. Chem. Lett. 2009, 19(9), 2420–2428. DOI: 10.1016/j.bmcl.2009.03.069.
   PubMed Web of Science ®Google Scholar
• Galal, S. A.; All, E.; Hegab, K. H.; Magd-El-Din, A. A.; Youssef, N. S.; El-Diwani, H. Novel antiviral benzofuran-transition metal complexes. Eur. J. Med. Chem. 2010, 45(7), 3035–3046. DOI: 10.1016/j.ejmech.2010.03.034.
   PubMed Web of Science ®Google Scholar
• Malpani, Y.; Achary, R.; Kim, S. Y.; Jeong, H. C.; Kim, P.; Han, S. B.; Kim, M.; Lee, C.-K.; Kim, J. N.; Jung, Y.-S. Efficient synthesis of 3H,3'H-spiro[benzofuran-2,1'-isobenzofuran]-3,3'-dione as novel skeletons specifically for influenza virus type B inhibition. Eur. J. Med. Chem. 2013, 62, 534–544. DOI: 10.1016/j.ejmech.2013.01.015.
   PubMed Web of Science ®Google Scholar
• Gündoğdu-Karaburun, N.; Benkli, K.; Tunali, Y.; Uçucu, U.; Demirayak, S. Synthesis and antifungal activities of some aryl [3-(imidazol-1-yl/triazol-1-ylmethyl) benzofuran-2-yl] ketoximes. Eur. J. Med. Chem. 2006, 41(5), 651–656. DOI: 10.1016/j.ejmech.2005.12.013.
   PubMed Web of Science ®Google Scholar
• Ryu, C.-K.; Song, A. L.; Lee, J. Y.; Hong, J. A.; Yoon, J. H.; Kim, A. Synthesis and antifungal activity of benzofuran-5-ols. Bioorg. Med. Chem. Lett. 2010, 20(22), 6777–6780. DOI: 10.1016/j.bmcl.2010.08.129.
   PubMed Web of Science ®Google Scholar
• Bandgar, B. P.; Patil, S. A.; Korbad, B. L.; Biradar, S. C.; Nile, S. N.; Khobragade, C. N. Synthesis and biological evaluation of a novel series of 2,2-bisaminomethylated aurone analogues as anti-inflammatory and antimicrobial agents. Eur. J. Med. Chem. 2010, 45(7), 3223–3227. DOI: 10.1016/j.ejmech.
   PubMed Web of Science ®Google Scholar
• Wu, S. F.; Chang, F. R.; Wang, S. Y.; Hwang, T. L.; Lee, C. L.; Chen, S. L.; Wu, C. C.; Wu, Y. C. Anti-inflammatory and cytotoxic neoflavonoids and benzofurans from Pterocarpus santalinus. J. Nat. Prod. 2011, 74(5), 989–996. DOI: 10.1021/np100871g.
   PubMed Web of Science ®Google Scholar
• Hu, Z. F.; Chen, L. L.; Qi, J.; Wang, Y. H.; Zhang, H.; Yu, B. Y. Two new benzofuran derivatives with anti-inflammatory activity from Liriope spicata var. prolifera. Fitoterapia. 2011, 82(2), 190–192. DOI: 10.1016/j.fitote.2010.09.002.
   PubMed Web of Science ®Google Scholar
• Yadav, P.; Singh, P.; Tewari, A. K. Design, synthesis, docking and anti-inflammatory evaluation of novel series of benzofuran based prodrugs. Bioorg. Med. Chem. Lett. 2014, 24(10), 2251–2255. DOI: 10.1016/j.bmcl.2014.03.087.
   PubMed Web of Science ®Google Scholar
• Carter, G. A.; Chamberlain, K.; Wain, R. L. Antifungal activity of isoflavonoids against storage fungi of the genus Aspergillus. Ann. Appl. Biol 1978, 88(1), 57–64. DOI: 10.1016/0031-9422(89)80338-3.
   Google Scholar
• Zacchino, S.; Rodriguez, G.; Pezzenati, G.; Orellana, G.; Enriz, R.; Gonzalez, S. M. In vitro evaluation of antifungal properties of 8.O.4‘-neolignans. J. Nat. Prod. 1997, 60(7), 659–662. DOI: 10.1021/np9605504.
   PubMed Web of Science ®Google Scholar
• Masataka, Y.; Mitsuru, N.; Takeshi, T.; Hideo, T. Synthesis of C-nucleosides via coupling of ribosyl fluoride with typical aromatic heterocycles bearing a TMS group. Heteroatom Chem. 1995, 6, 189. DOI: 10.1002/hc.520060214.
   Web of Science ®Google Scholar
• Yokoyama, M.; Akiba, T.; Togo, H. Synthesis of C-deoxyribonucleosides bearing typical aromatic heterocycles as base moiety. Synthesis. 1995, 1995(06), 638–640. DOI: 10.1055/s-1995-3969.
   Google Scholar
• Peyron, C.; Benhida, R. From intriguing reactivity of 2-bromothiophene to the first synthesis of C1'-disubstituted C-nucleosides. Synlett. 2009, 2009(03), 472–476. DOI: 10.1055/s-0028-1087537.
   Google Scholar
• Zhang, Q.; Sun, J.; Zhu, Y.; Zhang, F.; Yu, B. An efficient approach to the synthesis of nucleosides: gold(I)-catalyzed N-glycosylation of pyrimidines and purines with glycosyl ortho-alkynyl benzoates. Angew. Chem. Int. Ed. Engl. 2011, 50(21), 4933–4936. DOI: 10.1002/anie.201100514.
   PubMed Web of Science ®Google Scholar
• Zhang, F.; Wang, L.; Zhang, C.; Zhao, Y. Novel regio- and stereoselective phosphonyl radical addition to glycals promoted by Mn(ii)–air: syntheses of 1,2-dideoxy 2-C-diphenylphosphinyl glycopyranosides. Chem. Commun. (Camb). 2014, 50(16), 2046–2048. DOI: 10.1039/C3CC48806C.
   PubMed Web of Science ®Google Scholar
• Zhang, F.; Xi, Y.; Lu, Y.; Wang, L.; Liu, L.; Li, J.; Zhao, Y. Novel syntheses of aryl quinoxaline C-nucleoside analogs by mild and efficient three-component sequential reactions. Chem. Commun. (Camb). 2014, 50(43), 5771–5773. DOI: 10.1039/C4CC01448K.
   PubMed Web of Science ®Google Scholar
• Zhang, F.; Mu, D.; Wang, L.; Du, P.; Han, F.; Zhao, Y. Synthesis of substituted mono- and diindole C-nucleoside analogues from sugar terminal alkynes by sequential sonogashira/heteroannulation reaction. J. Org. Chem. 2014, 79(20), 9490–9499. DOI: 10.1021/jo501488x.
   PubMed Web of Science ®Google Scholar
• Zhou, X.; Jia, T.; Luo, Y.; Liu, H.; Zhang, F.; Zhao, Y. Concise synthesis of thiophene C-nucleoside analogues bearing sugar residues and aromatic residues through dimerization and sulfur heterocyclization of sugar alkynes and substituted iodoethynylbenzene. Org. Biomol. Chem. 2020, 18(9), 1800–1805. DOI: 10.1039/C9OB02717C.
   PubMed Web of Science ®Google Scholar
• Tronchet, J. M. J.; Gonzalez, A.; Zumwald, J. B.; Perret, F. Use of phosphorus ylides and sugar chemistry. XX. C-​glycosylic derivatives. XVIII. Synthesis of acetylenic sugars and rearrangement of the carbenoid intermediates. Helv. Chim. Acta. 1974, 57(6), 1505–1510. DOI: 10.1002/hlca.19740570605.
   Google Scholar
• Krishna, P. K.; Ayyagari, V. S. A new versatile strategy for C-aryl glycosides. Org. Lett. 2007, 9, 1121–1124. DOI: 10.1021/ol0701159.
   PubMed Web of Science ®Google Scholar
• Walton, D. J.; McPherson, J. D.; Hvidt, T.; Szarek, W. A. Synthetic routes to N-(1-deoxy-d-fructos-1-yl) amino acids by way of reductive amination of hexos-2-uloses. Carbohydr. Res. 1987, 167, 123–130. DOI: 10.1016/0008-6215(87)80273-2.
   Web of Science ®Google Scholar
• Dolhem, F.; Lievre, C.; Demailly, G. Synthesis of glyco-1-ynitols via 1,1-dibromo-1-alkenes from partially and unprotected aldoses. Tetrahedron. 2003, 59(2), 155–164. DOI: 10.1016/S0040-4020(02)01486-2.
   Web of Science ®Google Scholar
• Ayyagari, V. S.; Kalanidhi, P.; Krishna, P. K. Application of an enyne metathesis/Diels–Alder cycloaddition sequence: a new versatile approach to the syntheses of C-aryl glycosides and spiro-C-aryl glycosides. Chem. Eur. J. 2010, 16, 8545–8556. DOI: 10.1002/chem.201000482.
   PubMed Web of Science ®Google Scholar
• Sonogashira, K.; Thoda, Y.; Hagihara, N. A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines. Tetrahedron Lett. 1975, 50, 4467. DOI: 10.1016/S0040-4039(00)91094-3.
   Web of Science ®Google Scholar