Synthesis of (S)-mappicine and mappicine ketone via radical cascade reaction of isonitriles

(S)-Mappicine (2) and mappicine ketone (1) have been prepared from methylacetoacetate (4) by a strategy featuring a radical cascade reaction of an isonitrile as the key step. The introduction of the hydroxy group of (S)-mappicine occurred with moderate selectivity through asymmetric hydroxylation. (C) 1997 Elsevier Science Ltd.