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

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 o...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2017; no. 46; pp. 6906 - 6913
Main Authors Kipke, Andreas, Schöning, Kai‐Uwe, Yusubov, Mekhman, Kirschning, Andreas
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 15.12.2017
Wiley Subscription Services, Inc
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Summary: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. The TEMPO‐mediated oxidative deformylation of aldehydes was further developed for the preparation of chiral backbones with 1,2‐oxo functionalization found in polyketide antibiotics.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201701349