- Enantioselective synthesis of amino acids from pentacyclo[5.4.0.02,6.03,10.05,9] undecane-8,11-dione
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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.
- Martins, Frans J.C,Viljoen, Agatha M,Kruger, Hendrik G,Fourie, Louis,Roscher, Justus,Joubert, André J,Wessels, Philippus L
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