Synthesis of the aglycone of the shark repellent pavoninin-4 using remote functionalization |
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Authors: | Gong Hua Williams John R |
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Institution: | Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122-2585, USA. |
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Abstract: | reaction: see text] The aglycone of shark repellent pavoninin-4, (25R)-5alpha-cholestan-3alpha,15alpha,26-triol 26-acetate 1a, was synthesized from (25R)-cholest-5-en-3beta,26-diol 4 (26-hydroxycholesterol) in eight steps in 18% overall yield. Breslow's remote functionalization strategy was used as a key step to introduce the C-15alpha alcohol on a steroid D ring. An efficient synthesis of the 26-hydroxycholesterol from the 16beta hydroxyl steroid, (25R)-cholest-5-ene-3beta,16beta,26-triol (3a), is also reported. |
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