Synthesis of Epimeric 2-d_1-Dehydroepiandrosterones
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概要
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In order to clarify the metabolic fate of hydrogen at C-2 during microbial transformation of dehydroepiandrosterone into 1α-hydroxy-4-androstene-3,17-dione, the stereospecific synthesis of epimeric 2-d_1-dehydroepiandrosterones have been undertaken. A key intermediate leading to the required substrates, 5α-androst-2-ene-6β, 17β-diol 17-tert-butyl-dimethylsilyl ether, was prepared from dehydroepiandrosterone in several steps. Deuterioboration of the Δ^2-olefin and subsequent oxidation of the organoborane afforded the 2α-deuterio-3α-ol. The trans-diaxial opening of the 2α, 3α-epoxide with lithium aluminum deuteride provided the 2β-deuterio-3α-ol. Being submitted to dehydration with phosphorus oxychloride in pyridine followed by usual elaborations, the C-2 deuterated 6β-hydroxysteroids were converted to the desired 2-d_1-dehydroepiandrosterones.
- 公益社団法人日本薬学会の論文
- 1978-11-25
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