Highly efficient and scalable total syntheses and stereochemical assignment of potent anti-inflammatory pesimquinolones I and J

We report the synthesis and structural characterization of three crystalline borylated ortho-silylaryl trifluoromethanesulfonates: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trimethylsilyl)phenyl trifluoromethanesulfonate, C16H24BF3O5SSi (1a), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trimethylsilyl)phenyl trifluoromethanesulfonate, C16H24BF3O5SSi (1b), and 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trimethylsilyl)phenyl trifluoromethanesulfonate, C17H26BF3O5SSi (2), which are versatile aryne precursors. For all three compounds, the heteroatom substituents are almost coplanar with the central aromatic moiety. C—heteroatom bonding metrics are unexceptional and fall withing the typical range of C—B, C—Si, and C—O single bonds. Despite numerous electronegative sites, only weak intermolecular interactions are observed in the solid state.

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Highly efficient and scalable total syntheses and stereochemical assignment of potent anti-inflammatory pesimquinolones I and J

Abstract: Based on the goals of sustainability and environmentally conscious science, great progress has been made in the field of green chemical synthesis, but a synthesis that combines high levels of...

Cited by 2 publications

References 42 publications

Scalable total synthesis of aflaquinolone I and confirmation of the absolute configuration

Scalable total synthesis of aflaquinolone I and confirmation of the absolute configuration

Synthesis and crystal structures of boryl ortho-silylaryl trifluoromethanesulfonates

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