HAN Guang-dian (Han Kuang-tien), ZHU Li-ya. SYNTHESIS OF MAMMALIAN PHEROMONE 5α-ANDROST-16-EN-3-ONE AND 5α-ANDROST-16-EN-3α-OLJ. Acta Pharmaceutica Sinica, 1982, 17(9): 696-698.
Citation: HAN Guang-dian (Han Kuang-tien), ZHU Li-ya. SYNTHESIS OF MAMMALIAN PHEROMONE 5α-ANDROST-16-EN-3-ONE AND 5α-ANDROST-16-EN-3α-OLJ. Acta Pharmaceutica Sinica, 1982, 17(9): 696-698.
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SYNTHESIS OF MAMMALIAN PHEROMONE 5α-ANDROST-16-EN-3-ONE AND 5α-ANDROST-16-EN-3α-OL

    Abstract
  • The mammalian pheromone 5α-androst-16-en-3-one(Ⅰ) was synthesized from epiandrosterone(Ⅲ) via tosyl hydrazone(Ⅳ) followed by reduction with lithium aluminum hydride and oxidation with CrO3-H2SO4 reagent. 5α-Androst-16-en-3α-ol(Ⅱ) was obtained with the same partial approach from androsterone (Ⅶ), which can be prepared from epiandrosterone(Ⅲ) via the inversion of the configuration of the C3OH from its tosylate(Ⅵ) with sodium nitrite in DMF.
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