Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions

• Martyn Jevric,
• Julian Klepp,
• Johannes Puschnig,
• Oscar Lamb,
• Christopher J. Sumby and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2024, 20, 823–829, doi:10.3762/bjoc.20.74

• reports of Karban et al. (Scheme 2) [19]. We envisaged that these hexose-derived building blocks with a 2,5-anhydro bond such as 5 could be useful materials for the construction of C-nucleosides such as formycin A (Figure 1) [22][23][24]. The preparation of C-glycosides usually involves the creation of

Double-headed nucleosides: Synthesis and applications

• Vineet Verma,
• Jyotirmoy Maity,
• Vipin K. Maikhuri,
• Ritika Sharma,
• Himal K. Ganguly and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

Practical tetrafluoroethylene fragment installation through a coupling reaction of (1,1,2,2-tetrafluorobut-3-en-1-yl)zinc bromide with various electrophiles

• Ken Tamamoto,
• Shigeyuki Yamada and
• Tsutomu Konno

Beilstein J. Org. Chem. 2018, 14, 2375–2383, doi:10.3762/bjoc.14.213

• intriguing biological activities of CF2CF2-containing pyranose and furanose derivatives (Figure 1a) [7][8][9]. Subsequently, Gouverneur et al. also developed novel CF2CF2-containing C-nucleosides (Figure 1b) [10]. Meanwhile, in the field of materials sciences, Kirsch et al. revealed that the incorporation of

Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides

• Kartik Temburnikar and
• Katherine L. Seley-Radtke

Beilstein J. Org. Chem. 2018, 14, 772–785, doi:10.3762/bjoc.14.65

• , Baltimore, MD 21250, United States 10.3762/bjoc.14.65 Abstract C-nucleosides have intrigued biologists and medicinal chemists since their discovery in 1950's. In that regard, C-nucleosides and their synthetic analogues have resulted in promising leads in drug design. Concurrently, advances in chemical

• maneuver stereochemistry as well as to incorporate structural modifications. In this review, we describe recent reports on the modular synthesis of C-nucleosides with a focus on D-ribonolactone and sugar modifications that have resulted in potent lead molecules. Keywords: C-nucleosides; convergent

• . Replacing the hemiaminal (O–C–N) connectivity of the canonical nucleosides with an O–C–C bond (Figure 3) results in a class of compounds called “C-nucleosides” [45][46][47][48][49][50][51]. Further modification to a C–C–C connectivity results in “carbocyclic C-nucleosides” (Figure 3) [52][53]. C-nucleosides

Synthesis of ribavirin 2’-Me-C-nucleoside analogues

• Fanny Cosson,
• Aline Faroux,
• Jean-Pierre Baltaze,
• Jonathan Farjon,
• Régis Guillot,
• Jacques Uziel and
• Nadège Lubin-Germain

Beilstein J. Org. Chem. 2017, 13, 755–761, doi:10.3762/bjoc.13.74

• carbon atom in the 2’-position are an indium-mediated alkynylation and a 1,3-dipolar cyclization. Keywords: alkynylation; antiviral; cancer; C-nucleosides; ribavirin; Introduction The triazole nucleoside ribavirin (RBV, Figure 1) is used for the treatment of a number of viral infections and may be

• the combination, due to its particular role. Recently, we developed an alkynyl glycosylation protocol allowing us to obtain C-nucleoside derivatives and we turned our attention to ribavirin C-nucleoside analogues. Moreover, recently De Clerq [13] outlined the potential of C-nucleosides in the arsenal

Synthesis of rigid p-terphenyl-linked carbohydrate mimetics

• Maja Kandziora and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 1749–1758, doi:10.3762/bjoc.10.182

• are among the best methods to prepare C-arylglycosides, C-nucleosides and C-glycosidic oligomers when new artificial pharmacophores are approached [17]. With Suzuki cross-couplings C-glycoside analogues of phloriain with antidiabetic properties [18] or aryl-scaffolded dimers and trimers were

Multicomponent reactions in nucleoside chemistry

• Mariola Koszytkowska-Stawińska and
• Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

• asymmetric Biginelli reaction have been reviewed [97]. The reaction has been employed in the synthesis of C-nucleosides with 3,4-dihydropyrimidin-2(1H)-one or 3,4-dihydropyrimidin-2(1H)-thione as the nucleobase mimic. Up to date, depending on the role of the carbohydrate component in the reaction, C

• (77a), the aldehyde function (77b), or the β-ketoester function (77c) (Scheme 29) [101][102]. In contrast to the N-1-substituted homo-C-nucleosides 78, the C-4 or C-6-substituted C-nucleosides (i.e., compounds 79 or 80, respectively) were obtained with the diastereoisomeric excess varied from 33% to 50

• of the sugar aldehyde 77b or the sugar β-ketoester 77c, respectively. The debenzylated forms of C-nucleosides 78, 79 and 80 (as single diastereoisomers) were evaluated in vitro and in vivo as antimitotic agents [41]. They appeared to be less active than the reference (4S)-monastrol. Pyranose-derived