Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

• Haritha Sindhe,
• Malladi Mounika Reddy,
• Karthikeyan Rajkumar,
• Akshay Kamble,
• Amardeep Singh,
• Anand Kumar and
• Satyasheel Sharma

Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62

• partner under the reaction conditions c, branched alkylated products 41’ were obtained selectively in high yields (Scheme 9). A high functional group tolerance was observed in both linear and branched alkylated products. It is known that the strong coordination of the nitrogen atom in pyridine rings with

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

• Charlotte Collet,
• Françoise Chrétien,
• Yves Chapleur and
• Sandrine Lamandé-Langle

Beilstein J. Org. Chem. 2016, 12, 353–361, doi:10.3762/bjoc.12.39

• -alkylated and C-branched inositols and their corresponding fluoro analogues. The key steps of the synthesis were the easy accessibility of different types of arms in term of configuration (myo and scyllo), the linking method and length, which could modulate the biological properties. These inositol

• derivatives, bearing an arm terminated either with a hydroxy group or a fluorine atom, could be interesting candidates for diastereoisomeric intermediates and biological evaluations, especially for PET imaging experiments. Keywords: C-branched; diastereoselective; fluoroinositols; inositols; O-alkylated

• instance through radiolabeled compounds, seems judicious. Thus we planned to study new synthetic inositols of myo- and scyllo-configuration equipped with different carbon chains linked either on one hydroxy group, i.e., O-alkylated, or C-branched derivatives retaining the six hydroxy groups of the inositol

Synthesis of 1,2-cis-2-C-branched aryl-C-glucosides via desulfurization of carbohydrate based hemithioacetals

• Henok H. Kinfe,
• Fanuel M. Mebrahtu,
• Mandlenkosi M. Manana,
• Kagiso Madumo and
• Mokela S. Sokamisa

Beilstein J. Org. Chem. 2015, 11, 583–588, doi:10.3762/bjoc.11.64

• Henok H. Kinfe Fanuel M. Mebrahtu Mandlenkosi M. Manana Kagiso Madumo Mokela S. Sokamisa Department of Chemistry, University of Johannesburg, PO Box 524, Auckland Park 2006, South Africa 10.3762/bjoc.11.64 Abstract 1-C and 2-C-branched carbohydrates are present as substructures in a number of

• biologically important compounds. Although the synthesis of such carbohydrate derivatives is extensively studied, the synthesis of 1,2-cis-2-C-branched C-, S-, and N-glycosides is less explored. In this article a synthetic strategy for the synthesis of 1,2-cis-2-C-branched-aryl-C-glucosides is reported via a

• stereospecific preparation of 2,3-unsaturated-aryl-C-glycosides (Ferrier products). Keywords: aryl-C-glucoside; desulfurization; Ferrier product; hemithioacetal; Introduction 1-C (C-glycosides) and 2-C-branched carbohydrates are important carbohydrate analogues which have found wide application in

Concise total synthesis of two marine natural nucleosides: trachycladines A and B

• Haixin Ding,
• Wei Li,
• Zhizhong Ruan,
• Ruchun Yang,
• Zhijie Mao,
• Qiang Xiao and
• Jun Wu

Beilstein J. Org. Chem. 2014, 10, 1681–1685, doi:10.3762/bjoc.10.176

• ], exhibits significant cytotoxicity in vitro against several human cell lines such as leukaemia (CCRF-CEM, IC50 0.4 µg/mL), colon tumour (HCT-116, IC50 0.9 µg/mL), and breast tumour cells (MCF-7, IC50 0.2 µg/mL) [13]. Furthermore, such 2′-C-branched ribonucleosides are also potential agonists for adenosine

• synthesis of versatile 5′-deoxy-2′-C-branched nucleosides. Structures of trachycladine A and B. Retrosynthetic analysis of trachycladines A and B. The X-ray crystal structural of 1-O-methyl-3-O-(2,4-dichlorobenzyl)-5-deoxy-α-D-ribofuranose (9). Synthesis of 5-deoxy-1-O-acetyl-2,3-di-O-benzoyl-2-C-β-methyl-D

Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside

• Alafia A. Ansari,
• Y. Suman Reddy and
• Yashwant D. Vankar

Beilstein J. Org. Chem. 2014, 10, 300–306, doi:10.3762/bjoc.10.27

• , which has been well-explored for a variety of reactions in literature [37][38]. CAN was utilized successfully in carbohydrate chemistry for important transformations such as the azidonitration of glycals and the formation of 2-C-branched glycosides from glycals [39][40][41]. In this paper, we report on