A new direct synthesis of equilin from equilenin. Potassium–ammonia reduction of some non-conjugated double bonds

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Abstract
It is shown that the reduction of equilenin ethylene ketal with alkali metals in ammonia can be controlled to yield equilin ketal as the major product. With potassium at −33°, equilenin and equilin ketals are readily reduced to afford 8α-estrone ketals in good yield. Analogous reactions were observed with 2-naphthol.

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