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

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

Research School of Chemistry & Applied Biomedical Sciences

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	6906-6913
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	46
DOIs	https://doi.org/10.1002/ejoc.201701349
Publication status	Published - 15 Dec 2017

Keywords

Deformylation
Natural products
Polyketides
Radical reactions
TEMPO

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201701349

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title = "TEMPO-Mediated Oxidative Deformylation of Aldehydes: Applications in the Synthesis of Polyketide Fragments",

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.",

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AU - Yusubov, Mekhman

AU - Kirschning, Andreas

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AB - 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.

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KW - Natural products

KW - Polyketides

KW - Radical reactions

KW - TEMPO

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