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