Abstract
A new catalytic enantiospecific approach to the synthesis of epibrassinosteroids (and other polyhydroxylated steroids) regiospecifically labeled by heavy isotopes of hydrogen is reported. Chlorocarbonate, efficiently synthesized from α-hydroxy ketone by a reaction with triphosgene, undergoes reductive tritium dechlorination catalyzed by the [Pd0]/Et3N system, providing 24-[3β-3H]epicastasterone and 24-[3β-3H]epibrassinolide, respectively, in good yield and with high specific activity (5.8 Ci/mmol; 20% tritium enrichment per molecule).
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