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  • Title: Synthesis of the aglycone of the shark repellent pavoninin-4 using remote functionalization.
    Author: Gong H, Williams JR.
    Journal: Org Lett; 2006 May 25; 8(11):2253-5. PubMed ID: 16706499.
    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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