Extending pummerer reaction chemistry: (±)-dibromoagelaspongin synthesis and related studies

Ken S. Feldman, Matthew D. Fodor

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

The sponge-derived alkaloid dibromoagelaspongin was prepared from a dihydrooroidin derivative by exploiting the Pummerer reaction twice in succession. Oxidative cyclization of the substrate's pyrrole-2-carboxamide function into the imidazole moiety was achieved in a regiospecific manner to establish both C-N bonds to C(6) of the target.

Original languageEnglish (US)
Pages (from-to)3449-3461
Number of pages13
JournalJournal of Organic Chemistry
Volume74
Issue number9
DOIs
StatePublished - May 1 2009

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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