Studies on the mechanism of action of prekinamycin, a member of the diazoparaquinone family of natural products: Evidence for both sp2 radical and orthoquinonemethide intermediates

Ken S. Feldman, Kyle J. Eastman

Research output: Contribution to journalArticlepeer-review

49 Scopus citations

Abstract

The putative reductive activation chemistry of the diazoparaquinone antibiotics was modeled with Bu3Sn-H and prekinamycin dimethyl ether along with prekinamycin itself. Reaction in various combinations of aromatic solvents, with and without the nucleophile benzylmercaptan present, led to isolation of both radical-trapping arene adducts and nucleophilic capture benzyl thioether products. On the basis of these product distribution studies, the intermediacies of, first, a cyclopentenyl radical and, next, an orthoquinonemethide electrophile are postulated.

Original languageEnglish (US)
Pages (from-to)12562-12573
Number of pages12
JournalJournal of the American Chemical Society
Volume128
Issue number38
DOIs
StatePublished - Sep 27 2006

All Science Journal Classification (ASJC) codes

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

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