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

Antonio Rizzo, Dirk Trauner

Research output: Contribution to journalArticle

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

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Biomimetics
Streptomyces
Biological Products
cuprates
Anti-Bacterial Agents
nonanes
antibiotics
biomimetics
Substrates
assembly
rings
synthesis
products
enterocin
3-hydroxybutanal
nonane

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Toward (-)-Enterocin : An Improved Cuprate Barbier Protocol to Overcome Strain and Sterical Hindrance. / Rizzo, Antonio; Trauner, Dirk.

In: Organic Letters, Vol. 20, No. 7, 06.04.2018, p. 1841-1844.

Research output: Contribution to journalArticle

Rizzo, Antonio ; Trauner, Dirk. / Toward (-)-Enterocin : An Improved Cuprate Barbier Protocol to Overcome Strain and Sterical Hindrance. In: Organic Letters. 2018 ; Vol. 20, No. 7. pp. 1841-1844.
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