Synthetic investigation on testosterone and its analogues-II: syntheses of 8-iso-19-noranthratestosterone and 8-iso-10-iso-19-nortestosterone

The total synthesis of the anthracene analogue of 8-iso-19-nortestosterone has been described. dl-Dihydroequilenin and the ethylene ketal of d-equilenin have been converted to dl- and d-8-iso-17β-hydroxy-19-nor-and rost-5 (10)-en-3-one respectively, which were isomerized to dl- and d-8-iso-10-iso-19-nortestosterone, the ORD data of the latter confirming the configuration