Biomimetic Approach Toward Enterocin and Deoxyenterocin

Antonio Rizzo, Robert J. Mayer, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

Enterocin (vulgamycin) is a structurally remarkable natural product with significant antibiotic activity. The synthesis of a linear polyketide resembling a biosynthetic precursor was achieved using an unusual acyloin reaction. A diazo group was introduced as a protecting group for an enolizable ketone. We were unable to bring about the envisioned biomimetic aldol addition cascade and gained insights into the feasibility of this process by DFT calculations. As an alternative approach to enterocin, we developed a Cu-catalyzed intramolecular cyclopropanation followed by a MgI2-induced fragmentation to install the 2-oxabicyclo[3.3.1]nonane core of the natural product.

Original languageEnglish (US)
Pages (from-to)1162-1175
Number of pages14
JournalJournal of Organic Chemistry
Volume84
Issue number3
DOIs
StatePublished - Feb 1 2019

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Biomimetics
Biological Products
Polyketides
Ketones
Discrete Fourier transforms
Anti-Bacterial Agents
enterocin

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Biomimetic Approach Toward Enterocin and Deoxyenterocin. / Rizzo, Antonio; Mayer, Robert J.; Trauner, Dirk.

In: Journal of Organic Chemistry, Vol. 84, No. 3, 01.02.2019, p. 1162-1175.

Research output: Contribution to journalArticle

Rizzo, Antonio ; Mayer, Robert J. ; Trauner, Dirk. / Biomimetic Approach Toward Enterocin and Deoxyenterocin. In: Journal of Organic Chemistry. 2019 ; Vol. 84, No. 3. pp. 1162-1175.
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