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

Ken S. Feldman, Joshua F. Antoline

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)934-937
Number of pages4
JournalOrganic Letters
Volume14
Issue number3
DOIs
StatePublished - Feb 3 2012

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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