Synthesis and radiochemistry of 2,4-disubstituted 17 alpha-iodovinylestradiols.
This report details the preparation of three compounds which are structurally designed to have depressed metabolism and/or conjugation: 2,4-dibromo-, 2,4-dichloro-, and 2,4-dimethyl-17 alpha-iodovinylestradiol. Their synthesis includes the use of two novel transformations based upon tin chemistry: preparation of an intermediate 17 alpha-vinylstannanes via stannylcupration of a 17 alpha-ethynyl steroid, and preparation of the 2,4-dimethyl functionality via a palladium catalyzed coupling of 2,4-dibromoestrone acetate with tetramethyltin. The preparative radiochemistry of these three materials is also described.
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Organic Chemicals and Polymers Laboratory, Central Research and Development, Dow Chemical Company, Midland, MI 48674.
D004958:Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007457:Iodine Radioisotopes / Q000737:chemistry*; D007553:Isotope Labeling / Q000379:methods; D011854:Radiochemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis*
C092365:2,4-dibromo-17-iodovinylestradiol; C092364:2,4-dichloro-17-iodovinylestradiol; C092366:2,4-dimethyl-17-iodovinylestradiol; D007457:Iodine Radioisotopes; D014753:Vinyl Compounds; D004958:Estradiol; C034555:17 alpha-iodovinylestradiol