Diastereo- and enantiocontrolled synthesis of (-)-allosedamine via cycloaddition of a chiral nitrone

Article abstract of DOI:10.1002/hlca.19940770217

The piperidine alkaloid (-)-allosedamine (1) has been synthesized, in 21% overall yield, in nine steps starting from the formyl-ester 4. The synthesis features the reaction cascade 7 → 3 → 2, involving asymmetric electrophilic enolate hydroxyamination, hy