Synthesis of steroidal compounds and substances related to them 40. Synthesis of steroid analogs which do not contain ring b or c

1. The unsaturated bicyclic ketone (VIII) was obtained in 7% yield from the reaction of 2-bromomagnesium-6-methoxynaphthalene (I) with the methyl ether of dihydroresorcinol, and on being demethylated gave the model analog of homoequilenine (VII). 2. The reaction of p-anisylmagnesium bromide (X) with the methyl ether of dihydroresorcinol (II) led to the formation of 2-(p-methoxyphenyl)-Δ1-cyclohexen-6-one (XII) in 40% yield. 3. 6-(p-Hydroxy-o-methylphenyl)-1-tetrahydronaphthalone (XIX) was prepared by demethylation of 6-(p-methoxy-o-methylphenyl)-1-tetrahydronaphthalone (XX) with aluminum chloride in boiling xylene. 4. 6-(p-Hydroxyphenyl)-1-tetrahydronaphthalone (XXI) was converted into 6-(p-acetoxyphenyl)-1-tetrahydronaphthalone (XXIII) by boiling with acetic anhydride. 5. The tricyclic ketones (XXVII) and (XVIII) were isolated respectively by the action of the potassium derivative of 5-methoxy-2-tetrahydronaphmalone (XXVI) on 2-phenyl-1-bromoethane (XXIV) and 2-(m-methoxyphenyl)-1-bromoethane (XXV), and these after the cyclization with polyphosphoric acid and the subsequent dehydrogenation with palladium on carbon gave 1-methoxychrysene (XXXI) and 1,8-dimethoxychrysene (XXXII).