Ozonolysis of the Delta(8(14))-unsaturated steroids 1a,b afforded, instead of the expected 8,14-dioxo-8,14-seco derivatives 2a,b two stereoisomeric Delta(7)-unsaturated ozonides 3a,b and 4a,b.
Krstic, N., Declercq, J.-P., Lorenc, L., Pavlovic, V., Kalvoda, J., & Tinant, B. (2002). An unusual ozonolysis of the Delta(8(14))-unsaturated steroids. Journal of Chemical Research. Synopses, 8, 392-394. https://doi.org/10.3184/030823402103172428 (Original work published 2002)