SYNTHESIS OF (+/-)-[4A-ALPHA,4B-BETA,10B-BETA,12A-BETA]-9-HALOGENO-2-METHYL-1,2,3,4,4A,4B,5,6,10B,11,12,12A-DODECAHYDRONAPHTHO[2,1-F]-ISOQUINOLINES

Treatment of 5-(2-arylethyl)-1,2,3,4,5,6,7,8-octahydroisoquinolines with 48% HBr resulted in isomerisation of the double bond and subsequent cyclisation at position 6 of the octahydroisoquinoline ring system to give (+/-)-[4a alpha,4b beta,10b beta,12a beta]-9-halogeno-2-methyl-1,2,3,4,4a,4b,5,6,10b,11,12,12a-dodecahydronaphtho-[2,1-f]isoquinolines. The products obtained represent novel analogues of aza-D-homoestranes. No reaction was observed with the corresponding 5,5-disubstituted octahydroisoquinolines. An X-ray crystallographic study of compound 10 (X = Br) is described.