Studies towards the synthesis of (+)-ptilomycalin A; stereoselective N-acyliminium ion coupling reactions to enantiopure C-2 substituted lactams

Article abstract of DOI:10.1016/0040-4020(95)01085-8

Highly stereoselective N-acyliminium ion coupling reactions of β-ketoester derived silyl enol ethers with enantiopure lactams derived from (S)-malic acid are reported. This reaction type is applied in the synthesis of the enantiopure C-2 substituted lactam 27, a plausible intermediate in a projected synthesis of ptilomycalin A.