Secosteroids are compounds with cleaved bonds in the rings of the steroid skeleton. Apart from the well-known vitamins D, various structurally different secosteroids with diverse biological activities (antiproliferative, antiinflammatory, antimicrobial, antiviral, etc.) are found in Nature or have been prepared synthetically. A specific feature of secosteroids is the higher conformational flexibility of the macrocyclic ring in comparison with normal steroids and this may lead to a change in their biological properties. In this review several synthetic approaches are described, based on radical oxidation of the C5 and C14 tertiary alcohols and on Grob fragmentation.