Extending pummerer reaction chemistry. Application to the total synthesis of (±)-dibromoagelaspongin

Ken S. Feldman, Matthew D. Fodor

Research output: Contribution to journalArticle

38 Scopus citations

Abstract

The sponge metabolite dibromoagelaspongin was synthesized in 16 steps from imidazole. The route features two successive oxidative cyclizations with complete control of regiochemistry to deliver the unusual triaminomethane core of the target. These oxidative cyclizations likely resulted from Pummerer-like processes on the imidazole-2-sulfoxide (sulfide) precursors.

Original languageEnglish (US)
Pages (from-to)14964-14965
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number45
DOIs
StatePublished - Nov 12 2008

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Extending pummerer reaction chemistry. Application to the total synthesis of (±)-dibromoagelaspongin'. Together they form a unique fingerprint.

  • Cite this