The first synthesis of the furan-containing
snyderane, (+)-luzofuran,
is reported. The key step in this approach was an electrophilic brominative
cyclization, which was accomplished using a nucleophilic N-heterocycle-flanked phosphoramidite catalyst in combination with
the common laboratory reagent N-bromosuccinimide.
A side-product present in the herbicide pyroxasulfone was synthesized. The construction of a bis(aryloxy)fluoromethane moiety was necessary, for which no existing method was available. We report a simple, new procedure which we applied to the synthesis of some of these unusual structures.
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