163356-41-0Relevant academic research and scientific papers
Reaction of Sterols Containing the 7,14- or 8,14-Diene System with Ruthenium Tetroxide: Formation of Epoxysterols
Giordano, Federico,Piccialli, Vincenzo,Sica, Donato,Smaldone, Dina
, p. 501 - 525 (2007/10/02)
The reaction of ruthenium tetroxide with 5α-cholesta-8,14-dien-3β-yl acetate 2 and 5α-cholesta-7,14-dien-3β-yl acetate 7 has been performed using equimolar amounts of the oxidant in acetone-water at different temperatures (-70, -40 and -5 deg C).The former substrate furnished, along with the expected Δ8-14α-hydroxy-15-oxosteroid 3, the two related 8α,9α-epoxysterols 5 and 6 and the 8α,14α-epoxysterol 4 while the 7,14-diene steroid 7 afforded the two 8α,14α-epoxysterols 8 and 9 and the 14α,15α-epoxysterol 10.No unsaturated α-ketols were obtained in this case.The structure of 4 has been secured by single crystal X-ray crystallographic analysis.The increasing of the temperature causes a lowering in the overall yield of the oxidation products in both the reactions.These new results suggest that the reactivity of this oxidizing agent towards alkenes and conjugated dienes could be similar to that of the permanganate ion.
