<unk> , also known as 6,17α-dimethyl-6-dehydroprogesterone or as 6,17α-dimethyl-4,6-pregnadiene-3,20-dione, is a synthetic pregnane steroid and a derivative of progesterone. It is structurally related to the 17α-hydroxyprogesterone derivatives megestrol acetate and medroxyprogesterone acetate.<unk>  itself is not a 17α-hydroxyprogesterone derivative and is instead a derivative of 17α-methylprogesterone. This is because it features a methyl group at the C17α position instead of a hydroxy or acetoxy group. In addition to its C17α methyl group,<unk>  possesses a methyl group at the C6 position and a double bond between the C6 and C7 positions. The only structural difference between<unk>  and megestrol acetate is the replacement of the C17α acetoxy group with a methyl group. Synthesis The oral activity of 17α-methylprogesterone has already been alluded to. This compound, which may well owe this property to the inhibition of metabolism in a manner analogous to synthetic androgens and estrogens, is not sufficiently potent in its own right to constitute a useful drug. Incorporation of known potentiating modifications yields the commercially available oral progestin<unk>  (4). The preparation of the 6-methyl-16-dehydropregnenolone acetate (1) precursor is covered here.<unk>  synthesis. Reduction of the conjugated 16,17 double bond of 6-methyl-16-dehydropregnenolone acetate by means of lithium in liquid ammonia leads initially to the 17 enolate ion; this is alkylated in situ with methyl iodide. The now-familiar steric control asserts itself to afford the 17α-methyl compound,. The acetate group is lost as a side reaction. In an interesting modification on the usual scheme, (3) is treated with aluminum isopropoxide and a ketone (Oppenauer conditions) as well as chloranil in a single reaction; the 4,6-diene, (medrogesterone), is obtained directly from this step.
Medrogestone
Oxogestone
Phospho soda
Hermaphrodite 
Anagestone acetate
Medi-Cal
Diatrizoate
Lithotrite