Total synthesis of new pentacyclic heterocyclic steroidal analogs, 6-oxabenz[3,4]-d-homoestra 1,3,5(10),8,14-pentaen-17a-one and 3a,4,5,13-tetrahydro-3H-[2]benzothieno[5,4-d]naphtho[1,2-b]-pyran, from 4-oxa-1,2,3,4-tetrahydrophenanthren-I-one is described. © 1991.