Synthesis of the aglycone of 26-O-deacetyl pavoninin-5 |
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Authors: | John R Williams Deping ChaiJames D Bloxton II Hua GongWilliam R Solvibile |
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Institution: | Department of Chemistry, Temple University, Philadelphia, PA 19122-2585, USA |
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Abstract: | The aglycone of 26-O-deacetyl pavoninin-5, (25R)-cholest-5-en-3β,15α,26-triol, 5a, was synthesized in 10 steps in 17% overall yield from diosgenin, 3. Removing mercury from the Clemmensen reduction of diosgenin 3, gave a higher yield of (25R)-cholest-5-en-3β,16β,26-triol, 4, by a method, that is also more environmentally friendly. Attempted methods for the transposition of the C-16β hydroxyl to the 15α position are described. A successful method for this transposition via the 15α-hydroxy-16-ketone, 13, using the Barton deoxygenation reaction on the 16-alcohol, 15, is reported. |
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Keywords: | hydroxy steroids Pardachirus pavoninus shark repellent |
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