Novel stereoids from cetyltrimethylammonium permanganate-initiated oxidative rearrangements of 16-dehydroprogesterone

Article abstract of DOI:10.1016/S0040-4039(00)76637-8

Cetyltrimethylammonium permanganate initiates oxidative opening of the D-ring of 16-dehydroprogesterone in CH₂Cl₂. The novel steroids 3 and 4 have been isolated and characterized as the major products obtained from oxidative rearrangement of the steroid backbone. The X-ray crystal structure of the D-homosteroid 3 is provided, and a putative mechanism that invokes a benzilic acid rearrangement for formation of 3 is presented.