Palladium-Catalyzed Stereocontrolled Synthesis of Aryl-C-Glycosides from Arylboronic Acids and Glycal Enones Through 1,4-Conjugate Addition Reactions

Abstract

1,4-Conjugate addition of arylboronic acids to the glycal enones delivered 2-deoxy-α-aryl-C-glycosides in good yields. The reaction was catalyzed by palladium acetate in the presence of trifluoroacetic acid and 1,10-phenanthroline. A wide range of glycal enones derived from d-glucal, d-galactal, and d-rhamnal participated in the coupling reaction with different arylboronic acids smoothly. Different protecting groups including benzyl, acetyl, pivaloyl, and benzoyl were compatible under optimized conditions.

Key words

glycosides - aryl-C-glycosides - 2-deoxy-aryl-C-glycosides - glycal enones - synthetic methods

Publication History

Received: 29 August 2023

Accepted after revision: 21 September 2023

Accepted Manuscript online:
21 September 2023

Article published online:
06 November 2023

• References

• 1a Tripathi VD, Tripathi RP, Ramakrishna KK. G. Trends Carbohydr. Res. 2018; 10: 10
• 1b Whiting DA. Nat. Prod. Rep. 2001; 18: 583
• 1c Theriault RJ, Rasmussen RR, Kohl WL, Prokop JF, Hutch TB, Barlow GJ. J. Antibiot. 1986; 39: 1509
• 1d Shcherbako KV, Artemyeva MA, Burgart YV, Saloutin VI, Volobueva AS, Misiurina MA, Esaulkova YL, Sinegubova EO, Zarubaev VV. J. Fluorine Chem. 2020; 240: 109657
• 1e Nakatsuka T, Tomimori Y, Fukuda Y, Nukaya H. Bioorg. Med. Chem. Lett. 2004; 14: 3201
• 1f Wiley PF. J. Nat. Prod. 1979; 42: 569
• 1g Xiao J, Capanoglu E, Jassbi AR, Miron A. Crit. Rev. Food Sci. Nutr. 2016; 56: S29
• 2a Matsumoto T, Katsuki M, Jona H, Suzuki K. J. Am. Chem. Soc. 1991; 113: 6982
• 2b Kusumi S, Nakayama H, Kobayashi T, Kuriki H, Matsumoto Y, Takahashi D, Toshima K. Chem. Eur. J. 2016; 22: 18733
• 2c Tatsuta K, Ozeki H, Yamaguchi M, Tanaka M, Okui T. Tetrahedron Lett. 1990; 31: 5495
• 2d Kitamura K, Maezawa Y, Ando Y, Kusumi T, Matsumoto T, Suzuki K. Angew. Chem. Int. Ed. 2014; 53: 1262
• 2e Kitamura K, Ando Y, Matsumoto T, Suzuki K. Chem. Rev. 2018; 118: 1495
• 2f Yang Y, Yu B. Chem. Rev. 2017; 117: 12281
• 2g Bililign T, Griffith BR, Thorson JS. Nat. Prod. Rep. 2005; 22: 742
• 2h Rohr J, Thiericke R. Nat. Prod. Rep. 1992; 9: 103
• 3a Postema MH. D. Tetrahedron 1992; 48: 8545
• 3b Suzuki D, Matsumoto T. Total Synthesis of Aryl C-Glycoside Antibiotics. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products. Lukacs G. Springer-Verlag; Berlin: 1993
• 3c Jaramillo C, Knapp S. Synthesis 1994; 1
• 3d Du Y, Linhardt RJ, Vlahov IR. Tetrahedron 1998; 54: 9913
• 3e Levy DE, Tang C. The Chemistry of C-Glycosides, Tetrahedron Organic Chemistry Series, Vol. 13. Elsevier; Amsterdam: 1995: 1-291
• 3f Xiong DC, Zhang LH, Ye XS. Org. Lett. 2009; 11: 1709
• 3g Tang S, Zheng Q, Xiong DC, Jiang S, Li Q, Ye XS. Org. Lett. 2018; 20: 3079
• 3h Mabit T, Siard A, Legros F, Guillarme S, Martel A, Lebreton J, Carreaux F, Dujardin G, Collet S. Chem. Eur. J. 2018; 24: 14069
• 4a Singh AK, Venkatesh R, Kandasamy J. Synthesis 2019; 51: 4215
• 4b Singh AK, Kandasamy J. Org. Biomol. Chem. 2018; 16: 5107
• 5 Singh AK, Kanaujiya VK, Tiwari V, Sabiah S, Kandasamy J. Org. Lett. 2020; 22: 7650
• 6 Benhaddou R, Czernecki S, Ville G. J. Org. Chem. 1992; 57: 4612
• 7 Ramnauth J, Poulin O, Bratovanov SS, Rakhit S, Maddaford SP. Org. Lett. 2001; 3: 2571
• 8 Singh AK, Kanaujiya VK, Tiwari V, Sabiah S, Kandasamy J. Org. Lett. 2020; 22: 76
• 9a Lu X, Lin S. J. Org. Chem. 2005; 70: 9651
• 9b Zhang S, Shi L, Ding Y. J. Am. Chem. Soc. 2011; 133: 20218
• 10a Yamamoto Y, Nishikata T, Miyaura N. Pure Appl. Chem. 2008; 80: 807
• 10b Wang D, Weinstein AB, White PB, Stahl SS. Chem. Rev. 2018; 118: 2636
• 10c Tomás-Mendivil E, Díeza J, Cadierno V. Catal. Sci. Technol. 2011; 1: 1605
• 11a Chennaiah A, Verma AK, Vankar YD. J. Org. Chem. 2018; 83: 10535
• 11b Kirschning A. J. Org. Chem. 1995; 60: 1228
• 11c Weinig HG, Passacantilli P, Colapietro M, Piancatelli G. Tetrahedron Lett. 2002; 43: 4613
• 12 Yalamanchili S, Miller W, Chen X, Bennett CS. Org. Lett. 2019; 21: 9646