Approaches to the Synthesis of Quassinoids

A range of hydrophenanthrene methyl ethers were subjected to Birch reduction, and the products converted into the epoxides (21), (26) and (27). These were treated with diethylaluminium cyanide, but useful products were not obtained from (21) or (26). However, epoxide (27) was converted into the hydroxy nitrile (28) and thence enone (30), a potentially useful intermediate for the synthesis of quassinoids.