200120-84-9Relevant academic research and scientific papers
The synthesis of a-homo-b-norandrostanes: The effect of a hydroxyl on the course of hydrogenation of the Δ9-double bond
Kasal, Alexander,Slavikova, Barbora,Kohout, Ladislav,Budesinsky, Milos
, p. 1631 - 1641 (2007/10/03)
Acetolysis of 6β-mesyloxy-5-methyl-19-nor-5β-steroids (e.g. 10) was proved to yield 4a-homo-7,19-dinor compounds (e.g. 9) with a hydroxy group in the position 4aα. Hydrogenation of these compounds affords 9β,10β-dihydro derivatives (e.g. 12) predominantly, corresponding 9α, 10α isomers (e.g. 13) are only formed in low yields. This sequence was used for the synthesis of analogues of androgen hormones 4aα-hydroxy-4aβ-methyl-4a-homo-7,19-dinor-5α,9β,10β- androstane-3,17-dione (27), 4aα,17β-dihydroxy-4aβ,17a-dirnethyl-4a-homo-7,19-dinor-5α, 9β,10β-androstan-3-one (28) and 4aα,17β-dihydroxy-4aβ-methyl-4a-homo-7,19-dinor-5α, 9β,10β-androstan-3-one (29).
