133123-16-7Relevant articles and documents
Preparation of Antiandrogenic 17-Hydroxy-3,6-cyclo-4-nor-3,5-seco-6β-androstan-3-one by Deoxygenation of the Corresponding 5-Hydroxy Derivatives
Polman, Jiri,Kasal, Alexander
, p. 127 - 132 (2007/10/02)
This paper reports on three alternative procedures for the preparation of antiandrogenic 17β-hydroxy-3,6-cyclo-4-nor-3,5-seco-6β-androstan-3-one 15.The key step represents the removal of the oxygen functional group from position 5 which was effected by radical deoxygenation of thioesters of type 13.The variant of choice was the deoxygenation of the 5-thioimidazole 29 prepared from diketone 5.The 3-keto group was selectively protected during hydride reduction by conversion into the corresponding silyl enol ether.