Syntheses of cholesta-5,7-diene-3.BETA.,25-diol and cholesta-5,7-diene-1.ALPHA.,3.BETA.,25-triol.
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Adducts of 3β-acetoxy- and 1α,3β-diacetoxy-23,24-dinorchola-5,7-dien-22-al (<B>7</B> and <B>14</B>) with 4-phenyl-3<I>H</I>-1,2,4-triazole-3,5-dione prepared by the ozonolysis of the corresponding adducts of ergosteryl acetate and 1α-acetoxyergosteryl acetate were transformed into 22-bromo-3β-tetrahydropyranyloxy- and 22-iodo-1α,3β-bis(tetrahydropyranyloxy)-23,24-dinorchola-5,7-diene (<B>11</B> and <B>26</B>). The halide derivatives (<B>11</B> and <B>26</B>) were coupled with 2-methyl-4-phenylsulfonyl-2-(tetrahydropyranyloxy)butane (<B>6</B>) to afford 23-phenylsulfonyl-3β,25-bis(tetrahydropyranyloxy)- and 23-phenylsulfonyl-1α,3β,25-tris(tetrahydropyranyloxy)cholesta-5,7-diene (<B>12</B> and <B>27</B>). The reductive desulfonylation and deprotection of the tetrahydropyranyl group of <B>12</B> and <B>27</B> provided the title compounds, cholesta-5,7-diene-3β,25-diol (<B>1</B>) and cholesta-5,7-diene-1α,3β,25-triol (<B>2</B>).
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