TEMPO-Mediated Oxidative Deformylation of Aldehydes: Applications in the Synthesis of Polyketide Fragments

Andreas Kipke, Kai Uwe Schöning, Mekhman Yusubov, Andreas Kirschning

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A TEMPO-mediated oxidative deformylation of aldehydes is reported that yields the TEMPO adducts, which can be further oxidized to the corresponding ketones. The focus of this work was on the optimization of a synthetic protocol for use in natural product synthesis, specifically for the preparation of chiral backbones with 1,2-oxo functionalization found in polyketide antibiotics. In addition, the oxidative deformylation was combined with the oxidation of the alcohol to the precursor aldehyde in a one-pot protocol.

Original languageEnglish
Pages (from-to)6906-6913
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number46
DOIs
Publication statusPublished - 15 Dec 2017

Fingerprint

Polyketides
aldehydes
Aldehydes
fragments
antibiotics
synthesis
Biological Products
Ketones
ketones
adducts
alcohols
Alcohols
Anti-Bacterial Agents
Oxidation
preparation
oxidation
optimization
products
TEMPO
tempamine

Keywords

  • Deformylation
  • Natural products
  • Polyketides
  • Radical reactions
  • TEMPO

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

TEMPO-Mediated Oxidative Deformylation of Aldehydes : Applications in the Synthesis of Polyketide Fragments. / Kipke, Andreas; Schöning, Kai Uwe; Yusubov, Mekhman; Kirschning, Andreas.

In: European Journal of Organic Chemistry, Vol. 2017, No. 46, 15.12.2017, p. 6906-6913.

Research output: Contribution to journalArticle

Kipke, Andreas ; Schöning, Kai Uwe ; Yusubov, Mekhman ; Kirschning, Andreas. / TEMPO-Mediated Oxidative Deformylation of Aldehydes : Applications in the Synthesis of Polyketide Fragments. In: European Journal of Organic Chemistry. 2017 ; Vol. 2017, No. 46. pp. 6906-6913.
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