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Allenyl azide cycloaddition chemistry: application to the total synthesis of (±)-meloscine.

ABSTRACT: The pentacyclic alkaloid (±)-meloscine was prepared in 19 steps through a reaction sequence that features a putative azatrimethylenemethane intermediate, generated through cascade cyclization of an allenyl azide substrate, to deliver the core azabicyclo[3.3.0]octadiene substructure. Subsequent manipulation of the peripheral functionality then delivered (±)-meloscine.

SUBMITTER: Feldman KS

PROVIDER: S-EPMC3272129 | biostudies-literature | 2012 Feb

REPOSITORIES: biostudies-literature

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Allenyl azide cycloaddition chemistry: application to the total synthesis of (±)-meloscine.

Feldman Ken S KS Antoline Joshua F JF

Organic letters 20120113 3

The pentacyclic alkaloid (±)-meloscine was prepared in 19 steps through a reaction sequence that features a putative azatrimethylenemethane intermediate, generated through cascade cyclization of an allenyl azide substrate, to deliver the core azabicyclo[3.3.0]octadiene substructure. Subsequent manipulation of the peripheral functionality then delivered (±)-meloscine. ...[more]

PMID: 22242696

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