J. C. Orr, M. L. Franco, A. D. Cross
1964
Citations
0
Influential Citations
4
Citations
Journal
Steroids
Abstract
Abstract Reaction of 2-formyl-5α-androst-2-en-17β-ol (III) with ethynylmagnesium bromide yielded the ethynyl-ethylenic diol (IV). This diol was rearranged by means of sulfuric acid to the conjugated ethynyl-ethylenic diol (VIa), containing the 3-hydroxyl group in the α-configuration as evidenced by nuclear magnetic resonance spectroscopy. Other products obtained from (IV) by treatment with acid are the saturated hydroxydione (V), the methylfuran (VII) and the conjugated hydroxy-dienone (VIII). Some oxidation experiments carried out with the unconjugated diol (IV) and the conjugated diol (VIa) are described.