A Simple Acid-Catalyzed Isomerization of &γ-Hydroxy Enones into &γ-Diones

Article abstract of DOI:10.1021/jo00215a011

The acid-catalyzed isomerization of γ-hydroxy α,β-unsaturated ketones into γ-diones can be performed in high yields by using hydrogen bromide in ether.The utility of this functional group transformation is illustrated by its application to the synthesis of key intermediates 12a and 12b for rearranged drimanes, in steroid functionalization, and in the total synthesis of (+/-)-7-hydroxycostal.