Details
| Original language | English |
|---|---|
| Pages (from-to) | 6906-6913 |
| Number of pages | 8 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2017 |
| Issue number | 46 |
| Publication status | Published - 15 Dec 2017 |
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.
Keywords
- Deformylation, Natural products, Polyketides, Radical reactions, TEMPO
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, Vol. 2017, No. 46, 15.12.2017, p. 6906-6913.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - TEMPO-Mediated Oxidative Deformylation of Aldehydes
T2 - Applications in the Synthesis of Polyketide Fragments
AU - Kipke, Andreas
AU - Schöning, Kai Uwe
AU - Yusubov, Mekhman
AU - Kirschning, Andreas
N1 - Funding information: M. Y. thanks the Deutsche Akademische Austauschdienst (DAAD) and the Russian Science Foundation (RSF-16-13-10081) for financial support.
PY - 2017/12/15
Y1 - 2017/12/15
N2 - 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.
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.
KW - Deformylation
KW - Natural products
KW - Polyketides
KW - Radical reactions
KW - TEMPO
UR - http://www.scopus.com/inward/record.url?scp=85038076594&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201701349
DO - 10.1002/ejoc.201701349
M3 - Article
AN - SCOPUS:85038076594
VL - 2017
SP - 6906
EP - 6913
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 46
ER -