Investigations on sterols XXI^†: An alternative route for the synthesis of some 6-dehydro-9β,10α-steroid hormone analogues

Selective ozonisation of isolumisterone produced 9β,10α-bisnorchola-4,6-dien-3-on-22-al. This compound could be converted into: 6-dehydro-9β,10α-progesterone (9β,10α-pregna-4,6-diene-3,20-dione); 6-dehydro-17α-hydroxy-9β,10α-progesterone (9β,10α-pregna-4,6-dien-17α-ol-3,20-dione) and 6-dehydro-9β,10α-testosterone (9β,10α-androsta-4,6-dien-17β-ol-3-one).