Selective deuterium labeling of steroidal estrogens |
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Authors: | John H Block Carl Djerassi |
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Institution: | Department of Chemistry, Stanford University, Stanford, California 94305 USA |
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Abstract: | Refluxing estrone () and equilenin () in methanol-OD under basic conditions places a deuterium atom at position 4 and 16, and for estradiol at position 4. The location of the label in ring A is confirmed by nmr examination of the aromatic protons. Milder procedures that can be used for labeling the and positions of phenol and the cresols were not successful among steroids. Using palladized charcoal and deuterium, the benzylic hydrogens of estrone can be exchanged. Following the same procedure, but using hydrogen for a back exchange, one deuterium atom remains at position 6 as shown by C13 nmr spectroscopy. |
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