C-Glycosides are carbohydrates that bear aC ÀC bond to an aglycon at the anomeric center.D ue to their high stability towardsc hemical and enzymatic hydrolysis,t hese compounds are widely used as carbohydrate mimics in drug development. Herein, we report ag eneral and exclusively bselective method for the synthesis of anaturally abundant acyl-C-glycosidic structural motif first found in the scleropentaside natural product family.ACorey-Seebachu mpolung reaction as the key step in the synthesis of scleropentaside Aa nd analogues enables the b-selective construction of the anomeric C À Cb ond starting from unprotected carbohydrates in only four steps.T he one-pot approach is highly atom-efficient and avoids the use of toxic heavy metals.
The two marine natural products rubrolide R (1) and S (2) were synthesised in only three linear steps starting from commercially available tetronic acid without using protecting‐group chemistry. Key steps in the syntheses were the Pd‐catalysed Suzuki–Miyaura cross‐coupling followed by a vinylogous aldol condensation. Both compounds have been tested for their antibiotic and antiviral activities. At a concentration of 10 µm rubrolide R (1) and S (2), a 2‐log and 1.5‐log reduction in virus titre has been detected for a seasonal influenza virus (H3N2) and the pandemic swine influenza virus (pH1N1), respectively.
Diorcinols and related prenylated diaryl ethers were reported to exhibit activity againstm ethicillin-resistant clinicali solates of Staphylococcus aureus (MRSA). Within these lines, we report the first total synthesis of diorcinol D, I, J, the proposed structure of verticilatin and recently isolated antibacterial diaryl ether by using an efficient and highly divergent synthetic strategy.T hese total syntheses furnish the diaryl ethers in only five to seven steps employingaPd-catalyzed diaryl ether coupling as the key step. The total synthesis led to the structural revision of the natural product verticilatin, which has been isolated from ap lant pathogenic fungus. Furthermore, these structures were tested in order to determine their antibacterial activities against different MRSA strains as well as furtherGram-positive and-negative bacteria.
C-Glycosides are commonly used as carbohydrate mimics in drug development due to their stability against enzymatic and chemical hydrolysis. In this Synpacts article we elaborate on our fast and efficient β-selective approach towards protected and unprotected acyl glycosides. Application of a Corey–Seebach umpolung reaction enables the exclusive formation of the β-anomer of aromatic acyl-C-glycosides in good to excellent yields.1 Introduction2 C-Glycosylation of Benzylated Glycosyl Donors3 C-Glycosylation of Silylated Glycosyl Donors4 Conclusion
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