STEROIDS - Structure and Chemical Reactivity
by Alan Tonge as part of the VChemLab Project

Steroids are naturally-occurring substances of both plant & animal origin which have considerable medical importance -

*Digitoxigenin is actually the aglycon (non-sugar) component left after hydrolysis of the 3-trihexose parent Digitoxin

Most mammalian steroids are derived from Cholesterol. Despite a recent bad press, it is in fact an essential cellular component in mammals (the average human adult carries about 250g) and undergoes further biosynthetic transformations - part of the C17-sidechain is removed to give glucocorticoids, such as cortisol, and complete removal leads to the sex hormones testosterone & oestradiol.
Much of early steroid chemistry was developed on cholesterol - readily available from gallstones! Once the structure of the ring system had been solved - a fascinating chemical odyssey - the basic steroid skeleton proved particularly valuable for the development of theories of both reaction kinetics and reaction mechanism, providing a rigid framework upon which the effects of conformation and configuration could be explored.