We describe a concise synthesis of 4,4,10,16 tetra-desmethyl-1,2,3,4-t
etra-dehydro-16 alpha-hydroxystemodan-13-one which has the skeleton of
the diterpene stemodin using a trimethylsilyl ketyl radical / nitrile
cyclisation of 1,1-bis-cyanoethyl-2-tetralone as the key step. This c
ompound could be transformed to 4,4,10,16 tetra-desmethyl-1,2,3,4-tetr
a dehydro-16 alpha-hydroxyaphidicolane, which has the skeleton of aphi
dicolin via hydrogenation of the alkene derived from aprotic Bamford S
tevens elimination of an arylsulphonylhdydrazone derivative.