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Synthesis of dexamethasone labeled with carbon-14 and tritium

✍ Scribed by H. E. Mertel; A. M. Gerber; H. T. Meriwether

Publisher
John Wiley and Sons
Year
1970
Tongue
French
Weight
594 KB
Volume
6
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The syntheses of dexamethasone‐16α‐(methyl)‐^14^C and dexamethasone‐16β‐^3^H are described. Tritium labeling was achieved by catalytic addition of tritium to 3‐acetoxypregn‐16‐ene‐11,20‐dione, followed by bromination and dehydrobromination to give 3α‐acetoxy‐16‐^3^H‐pregn‐16‐ene‐11, 20‐dione. The stereochemistry of this sequence of reactions has been studied in detail. Carbon‐14 was introduced into the steroid nucleus by reaction of methyl‐^14^C‐magnesium iodide with 3α‐acetoxypregn‐16‐ene‐11,20‐dione. These tritium and carbon‐14 labeled intermediates were then carried through to the corresponding labeled dexamethasone by parallel reaction sequences.

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