The asymmetric synthesis of the conformationally constrained l- and d-lysine derivatives methyl (1 S,8 S)-1-amino-8-tert-butoxycarbonylamino-1,2,3,4,5,6,7,8-octahydroanthracene-1-carboxylate ( 4 ) and methyl (1 R,8 S)-1-amino-8-tert-butoxycarbonylamino-1,2,3,4,5,6,7,8-octahydroanthracene-1-carboxylate ( 5 ), respectively are described. Application of the Bucherer hydantoin synthesis to the carbonyl group of 2′,3′,4′,5′,6′,7′-hexahydrospiro[1,3-ethylenedithiole-2,1′-anthracen]-8′-one ( 18 ), which was prepared from 1,8-dichloroanthraquinone ( 14 ) in nine steps and the deprotection of the masked second ketone of 18 yields rac-21. The latter is the precursor for a novel asymmetric reductive amination protocol using ( R)-phenylglycinol as a chiral amino auxiliary and NaBH(OAc) 3 as a reducing agent. Using this procedure, the asymmetric reductive amination of α-tetralone derivatives and indanone proceeds with >95% de. Lower diastereomeric excesses are observed for benzosuberone (16.7% de) and acetophenone (27.3% de). rac-21 gave (1′ S,8′ S,1( R)- 25a (38% yield) and (1′ R,8′ S,1( R)- 25b (44.5% yield) with greater than 52 and 78% de, respectively. Cleavage of the amino auxiliary of (1′ S,8′ S,1( R)- 25a and of (1′ R,8′ S,1( R)- 25b with lead(IV) tetraacetate and hydrolysis of the hydantoin ring yields the unprotected analogs of 4 and 5 . The latter are transformed into the selectively protected target molecules 4 and 5 through standard protection procedures. The overall yield of the 17- and 18-step synthesis starting from 13 was 0.3% yield for each constrained lysine derivative.