Trichloroacetic acid-induced rearrangement of steroids. Aromatisation of 17-methyltestosterone into 1,2,10,15,16,17-hexahydro-10,17,17-trimethylcyclopenta[a]phenanthren-3-one

Abstract

1,2,10,15,16,17-Hexahydro-10,17,17-trimethylcyclopenta[a]phenanthren-3-one has been isolated from the action of trichloroacetic acid on methyltestosterone, and identified from its physical properties and comparison with synthetic phenanthrenones. A new route to 4,4a-dihydro-4a-methylphenanthren-2(3H)-one is described. Some aspects of the mechanism of the steroid rearrangement have been investigated.