The stereocontrolled synthesis of the water mold hormone (Z)-24(28)-dehydro-oogoniol and the Luche reduction of acyclic and cyclic alpha, beta-epoxy ketones

(Z)-24(28)-Dehydro-oogoniol, a steroid sex hormone isolated from the water mold Achyla (a primitive eukaryote), has been synthesized from dehydroadrenosterone in 24 steps with an overall yield of 8.1%. The reactions involved in this synthesis are highly regio- and stereoselective. The key steps include: (1) the CuCN-catalyzed addition of CH;The Luche reduction of both acyclic and cyclic...