Scientific article

Diastereo- and Enantiocontrolled Synthesis of (-)-Allosedamine via Cycloaddition of a Chiral Nitrone

Published inHelvetica Chimica Acta, vol. 77, no. 2, p. 554-560
Publication date1994

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.

Citation (ISO format)
VON OPPOLZER, Wolfgang, DEERBERG, Joerg, TAMURA, Osamu. Diastereo- and Enantiocontrolled Synthesis of (-)-Allosedamine <i>via</i> Cycloaddition of a Chiral Nitrone. In: Helvetica Chimica Acta, 1994, vol. 77, n° 2, p. 554–560. doi: 10.1002/hlca.19940770217
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Article (Published version)
ISSN of the journal0018-019X

Technical informations

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