Annulated Isoxazoles via [3
+ 2] Cycloaddition of
Alkenyl Bromides and Oximoyl Chlorides and Ag(I) Promoted Elimination
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Abstract
Substituted
salicylaldehydes are converted to fused tetracyclic
isoxazoles through a synthetic sequence incorporating substitution
of 2-bromo-2-cyclohexen-1-ol, formation of an oxime function, conversion
to an oximoyl chloride, intramolecular [3 + 2] cycloaddition, and
elimination of an equivalent of hydrogen bromide using silver(I) carbonate.
Six examples of this sequence are presented