Functionalisation of saturated hydrocarbons. Part 3. The oxidation of 3β,5α,6β-triacetoxycholestane using the Gif system

Abstract
The minor products from the oxidation of 3β,5α,6β-triacetoxycholestane using the Gif System [iron cluster–metallic zinc–pyridine–(aqueous) acetic acid–triplet oxygen] have been identified. The nature of the side-chain fragmentation to give 20-ketones has been clarified. Some mechanistic explanation has been offered for this unusual process.