184. Diastereo- and Enantiocontrolled Synthesis of (-)-Allosedamine via Cycloaddition of a Chiral Nitrone
     Oppolzer, W.; Deerberg, J.; Tamura, O.
     Helv. Chim. Acta 1994, 77, 554-560

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, hydroxylamine/aldehyde condensation, and nitrone/styrene cycloaddition, as well as the reductive N/O cleavage-decyanation 12 → 1.

DOI : 10.1002/hlca.19940770217 

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