Total synthesis of dl-19-nor-16,17-dehydroprogesterone.
dl-2-(7,11-Dimethyl-3,7,11 - trans,trans-dodecatrienyl)-3-methyl-cyclopent-2-enol was prepared by reduction of the corresponding ketone. This tetraenol, on treatment with trifluoroacetic acid, underwent stereoselective cyclization to give dl-3,17-dimethyl-A-nor-D-homoestra-3,16-diene. This tetracyclic material was readily converted, by oxidative cleavage to the bicyclic triketo aldehyde followed by a double aldol cyclization, into dl-19-nor-16,17-dehydroprogesterone.
D055598:Chemical Phenomena; D002621:Chemistry; D011374:Progesterone / Q000138:chemical synthesis*
D011374:Progesterone