A Convenient Synthesis of Cholesta-1,5,7-trien-3β-ol

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  • A convenient synthesis of cholesta-1,5,7-trien-3.BETA.-ol.

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Cholesta-4,6-dien-3β-ol (4) was obtained selectively by the dehydrobromination of 7-bromocholesterol with a base in the presence of a catalytic amount of tetrabutylammonium bromide. The oxidation of 4 with 2,3-dichloro-5,6-dicyano-p-benzoquinone gave cholesta-1,4,6-trien-3-one (7). Treatment of 7 with isopropenyl acetate under acidic conditions afforded 3-acetoxy-1,3,5,7-cholestatetraene, which was reduced with calcium borohydride to yield cholesta-1,5,7-trien-3β-ol (2).

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