Steroids. V. Conjugated steroid nitriles via phosphonates (1,2) |
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| Authors: | A K Bose R M Ramer |
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| Affiliation: | 1. College of Life Sciences, Qingdao Agricultural University, Qingdao 266109, China;2. CAS Key Laboratory of Marine Ecology and Environmental Sciences, Institute of Oceanology, Chinese Academy of Sciences, Qingdao 266071, China;3. Laboratory for Marine Ecology and Environmental Science, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266237, China;4. Center for Ocean Mega-Science, Chinese Academy of Sciences, Qingdao 266071, China;5. CAS Engineering Laboratory for Marine Ranching, Institute of Oceanology, Chinese Academy of Sciences, Qingdao 266071, China;6. Zhongke Tonhe (Shandong) Marine Technology Co., Ltd, Dongying 257200, China;1. Medical Oncology Department, Fondazione IRCCS Istituto Nazionale dei Tumori di Milano, Milan, Italy;2. Department of Pharmaceutical Sciences, Università degli Studi del Piemonte Orientale ''Amedeo Avogadro'', Novara, Italy;3. Department of Oncology and Hematology, Humanitas Clinical and Research Center, Rozzano, Italy;4. Laboratory of Methodology for Biomedical Research, IRCCS Mario Negri Institute for Pharmacological Research, Milan, Italy;5. Department of Experimental Oncology and Molecular Medicine, Fondazione IRCCS Istituto Nazionale dei Tumori di Milano, Milan, Italy;6. Fondazione Istituto FIRC di Oncologia Molecolare (IFOM), Milan, Italy;7. Dipartimento di Scienze Biomediche per la Salute, University of Milan, Milan, Italy;8. Department of Oncology and Hemato-oncology, University of Milan, Milan, Italy |
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| Abstract: | Steroid ketones were found to react with diethyl cyanomethylphosphonate in the presence of dimsyl anion and dimethyl sulfoxide at room temperature forming conjugated nitriles. Ketones at positions 2,4,6,7,12, and 15 readily afforded unsaturated nitriles. The yield of Δ4-3-cyano-methylene steroids from Δ4-3-ketosteroids was high under these conditions. The sterically hindered ketone from lanosterol also could be converted to an unsaturated nitrile.Ketones at positions 1 and 11 were found to be unreactive even when dimsyl anion and dimethyl sulfoxide were used. 16-Ketoprogesterone did not react, probably because it is a β-diketone. |
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