Title of article :
Enantioselective synthesis of amino acids from pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione
Author/Authors :
Frans J.C Martins، نويسنده , , Agatha M Viljoen، نويسنده , , Hendrik G Kruger، نويسنده , , Louis Fourie، نويسنده , , Justus Roscher، نويسنده , , André J Joubert، نويسنده , , Philippus L Wessels، نويسنده ,
Abstract :
Treatment of (+)-pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8-one with sodium cyanide and ammonium carbonate produced an optically active hydantoin of which the 4′-carbonyl group of the hydantoin ring is in the less sterically hindered equatorial position. Hydrolysis of the latter with barium hydroxide produced (−)-8-amino-pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8-carboxylic acid which has the 1S,2R,3R,5R,6R,7S,8R,9R,10R configuration. In a similar way, (+)-6-amino-tetracyclo-[6.2.0.04,11.05,9]undec-2-ene-6-carboxylic acid with 1R,4R,5R,6R,8S,9S,11R configuration was obtained from (−)-tetracyclo[6.3.0.04,11.05,9]undec-2-ene-6-one. The latter was obtained from (−)-11-hydroxy-pentacyclo[5.4.0.02,6.03,10.05,9]undecan-8-one.
