Synthesis of 25-hydroxycholesterol from 3β-hydroxyandrost-5-en-17-one. A method for stereospecific construction of a sterol side-chain
Abstract
The side-chain of 25-hydroxycholesterol was constructed stereospecifically on the androstane skeleton via addition of an ethyl acetate unit to C-17 and sub-sequent alkylation of the resulting ester C-20 with a C5 unit; the remaining carbon atom (C-27) was added by a Grignard reaction.