Ozonolysis of the Δ8(14)-unsaturated steroids 1a,b afforded, instead of the expected 8,14-dioxo-8,14-seco derivatives 2a,b two stereoisomeric Δ7-unsaturated ozonides 3a,b and 4a,b.
Prepared by acid-catalyzed isomerisation of 5α-androst-7-ene-3β,17β-diyl diacetate. Unpublished results.
3.
The olefinic Δ8(14)-bond in 1a was successively cleaved with ruthenium tetroxide1.
4.
A list of the fractional atomic coordinates, isotropic thermal parameters and bond lengths and angles has been deposited at the Cambridge Crystallographic Data Centre as supplementary publication No 172508.
