THE SYNTHESIS OF (+)-3-METHOXY-7-ALPHA-METHYL-17-ALPHA-CYANOMETHYL-17-BETA-HYDROXY-1,3,5(10)-ESTRATRIENE

The titled compound 12 was obtained through seven steps using the compound 3 as starting material. Hydrogenated compound 4 obtained from 8 was cyclized with H2SO4 to the compound 6, hydrogenation of which gave a mixture of the compound 7 and 8. The compound 8 was also secured directly by reduction of 6 with Li and liq. NH3. Deprotection of the compound 8 by HCl gave the compound 9 which was oxidized to the compound 10. Introducing the methylene group by dimethyl oxosulfonium methylide at 17-ketone in the compound 10 gave the epoxide 11 which was cleavaged to the titled compound 12 by NaCN.