PubMed · 14033121
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R W KISTNER. 1963. New steroid compounds with progestational activity.. https://pubmed.ncbi.nlm.nih.gov/14033121/
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18-Hydroxy-6,19-oxidoprogesterone and 18-hydroxy-11, 19-oxidoprogesterone were synthesized from readily available materials. The functionalization of C-18 was accomplished with phenyliodosodiacetate/iodine, whereas that of C-19 was carried out with the mercuric oxide/iodine system, both under irradiation with visible light. For 18-hydroxy-11,19-oxidoprogesterone, C-19 was functionalized before C-18, whereas the reverse order had to be used for the 6,19-oxido derivative.
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The mass spectral fragmentation of a number of 17alpha-hydroxy-, 17alpha-acetoxy-, and 17alpha-methoxyprogesterones have been examined. Unlike other steroidal delta4-3-ketones, fragmentation reactions associated with the alpha,beta-unsaturated ketonic function are not particularly significant; rather, abundant ions are formed by decomposition processes occurring in and around ring D. Reactions of diagnostic significance include complete or partial loss of ring D, and elimination of the C-17 side chain (CH3CO), followed by loss of the C-17 oxygen function together with a hydrogen atom (H2O, CH3COOH, CH3OH).