Enantioselective synthesis of amino acids from pentacyclo[5.4.0.0 2,6.0 3,10.0 5,9]undecane-8,11-dione

Treatment of (+)-pentacyclo[5.4.0.0 2,6.0 3,10.0 5,9]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 hydr...

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Bibliographic Details
Published in:Tetrahedron 2001-02, Vol.57 (8), p.1601-1607
Main Authors: Martins, Frans J.C, Viljoen, Agatha M, Kruger, Hendrik G, Fourie, Louis, Roscher, Justus, Joubert, André J, Wessels, Philippus L
Format: Article
Language:English
Subjects:
amino acids
cage compounds
stereoselection
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Summary:Treatment of (+)-pentacyclo[5.4.0.0 2,6.0 3,10.0 5,9]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[5.4.0.0 2,6.0 3,10.0 5,9]undecane-8-carboxylic acid which has the 1 S,2 R,3 R,5 R,6 R,7 S,8 R,9 R,10 R configuration. In a similar way, (+)-6-amino-tetracyclo-[6.2.0.0 4,11.0 5,9]undec-2-ene-6-carboxylic acid with 1 R,4 R,5 R,6 R,8 S,9 S,11 R configuration was obtained from (−)-tetracyclo[6.3.0.0 4,11.0 5,9]undec-2-ene-6-one. The latter was obtained from (−)-11-hydroxy-pentacyclo[5.4.0.0 2,6.0 3,10.0 5,9]undecan-8-one. Amino acids were obtained via hydantoin intermediates.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)01140-6