Regioselective Synthesis of Two Novel 2-geranyloxyacetophenones

The phenols containing geranyl units¹ are a large group of interesting natural products exhibited many physiological actions as antiflammatory, antibacterial and antioxidative activities². Two novel acetophenones 1 and 2 were recently isolated from the fruits of Evodia merrillii, a small folk medicinal tree widely distributed in Taiwan³. Their structures were elucidated as 2-(1'-geranyl)-4,6-dihydroxyacetophenone 1 and 2-(1'-geranyloxy)-2,6,α-trihydroxyacetophenone 2 by means of spectroscopic data. So far as we know, the total synthesis of them have not been reported yet. Herein, we wish to report the first total synthesis of 1 and 2,starting from 2,4,6-trihydroxyacetophenone.