Synthesis and Pyrogenic Effect of 3α,7α-Dihydroxy-5β-androstan-17-one and 3α-Hydroxy-5β-androstane-7,17-dione

Article abstract of DOI:10.1016/0039-128X(80)90041-0

The first chemical synthesis of 3α,7α-dihydroxy-5β-androstan-17-one and 3α-hydroxy-5β-androstane-7,17-dione is reported.In this method, the 17β-side chain of commercial chenodesoxycholic acid was degraded in 6 steps after selective protection of the hydroxyl groups: 3α-OH by a tert-butyldimethylsilyl group and 7α-OH by an acetoxy group.The capacity of 3α,7α-dihydroxy-5β-androstan-17-one and 3α-hydroxy-5β-androstane-7,17-dione to release a pyrogen by human leukocytes was investigated by two independent methods: supernatants from leukocytes incubated with a steroid are injected to rabbits whose fever is measured, or tested by the Limulus Test (a pyrogen detection technique).The 7-keto substituted etiocholanolone still possessed pyrogenic activity, while the 7α-hydroxyl substituted one did not.