Synthesis studies on the Melodinus alkaloid meloscine

Ken S. Feldman, Joshua F. Antoline

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

The pentacyclic Melodinus alkaloid (±)-meloscine was synthesized in 19 chemical steps from 2-bromobenzaldehyde through a route featuring an allenyl azide cyclization cascade to deliver the core azabicyclo[3.3.0]octane substructure. Peripheral functionalization of this core included a Tollens-type aldol condensation to set the quaternary center at C(20) and a diastereoselective ring-closing metathesis to forge the tetrahydropyridine ring.

Original languageEnglish (US)
Pages (from-to)1434-1445
Number of pages12
JournalTetrahedron
Volume69
Issue number5
DOIs
StatePublished - Feb 4 2013

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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