Synthesis of 26-Halo-, 26-(Phenylseleno)-, and 26-Indolylcholesterol Analogues

Article abstract of DOI:10.1021/jo00327a025

Diosgenin was converted to 26-hydroxycholesterol.Treatment of the 26-hydroxycholesterol with (C6H5)3P and N-bromo- or N-iodosuccinimide gave the 26-bromide and 26-iodide, respectively.Alkylation of 3-methylindole with 26-bromocholesterol 3-silyl ether gave the 26-(3-methylindol-1-yl)cholesterol.Reaction of cholesta-5,25-dien-3β-ol acetate with phenylselenium bromide and potassium acetate gave 26-(phenylseleno)cholest-5-ene-3β,25-diol diacetate and 26-(phenylseleno)cholest-5-ene-3β,25-diol 3-acetate.