Kulkarni S, Abdel-Baky S, Le Quesne P W, Vouros P
Department of Chemistry, Northeastern University, Boston, MA 02115.
Steroids. 1989 Jan-Feb;53(1-2):131-47. doi: 10.1016/0039-128x(89)90150-5.
The reaction of trimethylsilylimidazole (TSIM) and 3-keto-5,10-epoxy-nor-19-methylandrostanone 3 and its 17-acetate analog 4 was examined at two different temperatures. In both compounds, reaction at 90 degrees C gave predominantly a delta 3-silyl-enol ether plus a minor product as a result of the epoxide ring opening. Under reflux conditions, besides the aforementioned products, aromatization of the A-ring was observed as a major process. The results suggest the potential use of silylation reactions with epoxyketones towards the synthesis of aromatic compounds.
在两个不同温度下研究了三甲基硅基咪唑（TSIM）与3-酮-5,10-环氧-去甲-19-甲基雄甾烷酮3及其17-乙酸酯类似物4的反应。在这两种化合物中，90℃下的反应主要生成δ3-硅烯醇醚以及由于环氧环开环产生的少量产物。在回流条件下，除了上述产物外，还观察到A环的芳构化是主要过程。结果表明，环氧酮的硅烷化反应在芳香族化合物的合成中具有潜在用途。
