Toward (-)-Enterocin: An Improved Cuprate Barbier Protocol to Overcome Strain and Sterical Hindrance

Antonio Rizzo, Dirk Trauner

Research output: Contribution to journalArticlepeer-review

Abstract

An approach toward (-)-enterocin, an antibiotic isolated from Streptomyces hygroscopicus, is described. Its compact, heavily oxidized protoadamantane core represents a daunting challenge for an efficient synthesis. Convergent assembly of its 2-oxabicyclo[3.3.1]nonane core with a cuprate-mediated Barbier reaction is disclosed. Its functionalization to a suitable substrate for a biomimetic aldol to close the final ring of the natural product is evaluated.

Original languageEnglish (US)
Pages (from-to)1841-1844
Number of pages4
JournalOrganic Letters
Volume20
Issue number7
DOIs
StatePublished - Apr 6 2018

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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