Diastereo- and Enantiocontrolled Synthesis of (-)-Allosedamine <i>via</i> Cycloaddition of a Chiral Nitrone

Von Oppolzer, Wolfgang; Deerberg, Joerg; Tamura, Osamu

doi:10.1002/hlca.19940770217

Scientific article

English

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

ContributorsVon Oppolzer, Wolfgang; Deerberg, Joerg; Tamura, Osamu

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

Publication date1994

Abstract

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.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang, DEERBERG, Joerg, TAMURA, Osamu. Diastereo- and Enantiocontrolled Synthesis of (-)-Allosedamine via Cycloaddition of a Chiral Nitrone. In: Helvetica Chimica Acta, 1994, vol. 77, n° 2, p. 554–560. doi: 10.1002/hlca.19940770217

Article (Published version)

Identifiers

PID : unige:151918
DOI : 10.1002/hlca.19940770217

Additional URL for this publicationhttp://doi.wiley.com/10.1002/hlca.19940770217

Journal ISSN0018-019X

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

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