Reductive cleavage of the 9,10-bond in 11-oxygenated steroids: a new method for the partial synthesis of the vitamin D skeleton

Abstract

11-Oxygenated steroids with a ring A dienone system are reduced in non-protic media with cleavage of the 9,10-bond, and the resulting 9,10-secosteriods (2) or (5) were converted into 9,10-secocholesta-1,3,5(10)-triene-3-ol (12), an unknown isomer of cholecalciferol (vitamin D3).