| Summary: | In this thesis it was shown that Isoallopregnanolone can be synthesized from Allopregnanolone by the Mitsunobu reaction as well as by oxidation with o-iodoxybenzoic acid (IBX) with subsequent reduction with NaBH 4. It was shown that the oxidation with subsequent reduction was a better method for synthesis in microgram scale. The oxidationreduction method was carried out in microgram scale on tritium labeled Allopregnanolone (Pregnane-3α-ol-20one, 5α[9,11,12- 3H(N)] to produce the corresponding tritium labeled Isoallopregnanolone. The possibility of synthesizing Tetrahydrodeoxycorticosterone (THDOC) from Allopregnanolone in microgram scale was examined. Formation of a silylenol ether analog of Allopregnanolone and subsequent oxidation with m-CPBA was examined as a method to synthesizing THDOC. The synthesis of THDOC by this procedure was found not to be efficient enough to be used in microgram scale
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