Abstract
12-Methyl B/C hexahydrobenzo[ c]phenanthridines have been synthesized stereoselectively starting from chiral nonracemic 2-aryl-4-pentenoic acids prepared by asymmetric allylation of (+)-( S,S)-pseudoephedrine-based arylacetamide enolates. Subsequent transformations (Friedel–Crafts acylation, stereocontrolled reductive amination, Pictet–Spengler cyclization and PPA catalyzed cationic cyclization) led to the synthesis of enantiomerically enriched hexahydrobenzo[ c]phenanthridines in which the sequential formation of all the new stereogenic centres was controlled by the starting chiral acids.
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