Total Synthesis of Nikkomycin S_z and Nikkomycin So_z

Abstract

The nikkomycins S z /So z are a class of locked nucleoside antibiotics that share a common [5,6] trans-bicyclic core. Herein we present an efficient synthesis of these nikkomycins from diene, using neighboring group participation N-glycosylation and stereoselective oxidation state installation. This synthetic strategy overcomes several challenges due to the poor redox tolerance of the uracil base, the high strain of the trans-fused furanopyran C8 monosaccharides, and the acid-sensitive glycosidic bond when dealing with the deoxynucleotide natural product nikkomycin S z .

Copper–Catalyzed Construction of the Indole Core: Recent Advancements

“…Assembly of N‐(2‐formylaryl) sulphonamides 129 , secondary amines 130 and solid calcium carbide 131 for synthesizing indole derivatives was investigated by Li and co‐workers [95] . The one‐pot three component reaction was conducted in the presence of CuBr (mediator), Na 2 CO 3 (base), water (promoter) in DMSO at 100 °C to furnish 2‐methylene‐3‐aminoindolines 132 .…”

Cu‐Catalyzed Synthesis of 4H‐benzo[4,5]thiazolo[3,2‐a]pyrimidin‐4‐ones: Molecular Docking Studies and Anti‐Proliferative Activities Against HepG2 Hepatocellular Carcinoma Cells

“…Recently, Beifuss and co‐workers reported the synthesis of pyrimidobenzothiazoles from the reaction of catechol and 2,3‐dihydro‐2‐thioxopyrimiden‐4(1 H )‐ones using Laccase catalyst. However, this route suffers from the formation of two regioisomers such as 2 H ‐pyrimido[2,1‐ b ]benzothiazol‐2‐ones and 4 H ‐pyrimido[2,1‐ b ]benzothiazol‐4‐ones, and the complicated separation technique of these products [29,52–53] . Consequently, there is still a need to develop simply accessible and mild method for the synthesis of pyrimidobenzothiazoles starting from a broad class of readily available monomers.…”