h3c o h3c o
Another way is to synthesize it from available androstenolone (dihydroepiandrosterone) (28.1.10), which in turn is made from dibromocholesterol acetate. Reduction of the double bond in androstenolone by hydrogen using a palladium on carbon catalyst gives a keto-alco-hol (28.1.11), which is further oxidized by chromium (VI) oxide to the diketone (28.1.12). This undergoes bromination by molecular bromine in acetic acid, giving a dibromide (28.1.13). The product undergoes dehydrobromination by heating it in collidine, which forms the dieneone (28.1.14). Upon heating this compound at a temperature of about 530 methane molecule detached from position 10 to form aromatic ring A and the desired estrone (28.1.9) is formed.
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