Studies on Steroidal Compounds. VII. Synthesis of 1α-Methyl Steroids.

摘要: The Grignard reaction of 5α-cholest-1-en-3-one (IIIa) in the presence cuprous chloride gave 1α-methyl-5α-cholestan-3-one (IVa). (IVa) was brominated and dehydrobrominated to give 1α-methylcholest-4-en-3-one (VIa). (VIa) hydrogenated over palladium-charcoal 1α-methyl-5β-cholestan-3-one (VII). Discussions were made on configuration C-1 methyl group. Similarly, 17β-hydroxy-5α-androst-1-en-3-one (IIIb) transformed into (IVb) (VIb).