Synthesis of exo-3-amino-10-hydroxy-hexacyclo[10.2.1.02,11.04,10.04,14.09,13]pentadecane-5,7-diene-endo-3-carboxyclic acid and endo-3-amino-10-hydroxy-hexacyclo[10.2.1.02,11.04,10.04,14.09,13]pentadecane-5,7-diene-exo-3-carboxylic acid

Treatment of hexacyclo[7.4.2.01,9.03,7.04,14.06,15]pentadecane-10,12-diene-2,8-dione with aqueous sodium cyanide produced 2,8-dihydroxy-hexacyclo[7.4.2.01,9.03,7.04,14.06,15]pentadecane-10,12-diene-2,8-lactam and with sodium cyanide, ammonium chloride and ammonium hydroxide, 2-amino-8-hydroxy-hexacyclo [7.4.2.01,9.03,7.04,14.06,15]pentadecane-10,12-diene-2,8-lactam was obtained. 10-Hydroxy-hexacyclo [10.2.1.02,11.04,10.04,14.09,13]pentadecane-5,7-diene-3-one was converted into the corresponding aminonitrile and hexacyclo[10.2.1.02,11.04,10.04,14.09,13]pentadecane-5,7-diene-10-hydroxy-3-spiro-5′-hydantoin. Treatment of the latter with barium hydroxide produced exo-3-amino-10-hydroxy-hexacyclo [10.2.1.02,11.04,10.04,14.09,13]pentadecane-5,7-diene-endo-3-carboxylic acid. The isomeric endo-3-amino-10-hydroxy-hexacyclo[10.2.1.02,11.04,10.04,14.09,13]pentadecane-5,7-diene-exo-3-carboxylic acid was obtained from 3-cyano-3-ureido-hexacyclo[10.2.1.02,11.04,10.04,14.09,13]pentadecane-5,7-diene-10-ol.