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

  • Feldman K
  • Antoline J
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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.

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  • Ken S. Feldman

  • Joshua F. Antoline

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