Details
| Original language | English |
|---|---|
| Pages (from-to) | 7998-8002 |
| Number of pages | 5 |
| Journal | Chemistry - a European journal |
| Volume | 26 |
| Issue number | 36 |
| Early online date | 18 Feb 2020 |
| Publication status | Published - 26 Jun 2020 |
Abstract
anti-Configured 1,3-dimethyl deoxypropionate motifs are important sub structures in natural products. Herein, we describe a bidirectional approach for the rapid construction of natural products featuring such motifs by using C2-symmetrical 1,3-bis(boronic esters). As for its application in convergent syntheses it was important to establish a selective mono-Zweifel olefination we describe the scope and limitations by using different 1,3-bis(boronic esters) and nucleophiles. This protocol takes advantage of the combination of the Hoppe–Matteson–Zweifel chemistry, which was elegantly put into practice by Aggarwal et al. In order to show its applicability the total syntheses of two natural products, serricornin and (+)-invictolide, were performed.
Keywords
- C-symmetry, desymmetrization, lithiation–borylation chemistry, mono-Zweifel olefination, natural product synthesis
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Chemistry - a European journal, Vol. 26, No. 36, 26.06.2020, p. 7998-8002.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Desymmetrization of C2-Symmetric Bis(Boronic Esters) by Zweifel Olefinations
AU - Linne, Yannick
AU - Schönwald, Axel
AU - Weißbach, Sebastian
AU - Kalesse, Markus
PY - 2020/6/26
Y1 - 2020/6/26
N2 - anti-Configured 1,3-dimethyl deoxypropionate motifs are important sub structures in natural products. Herein, we describe a bidirectional approach for the rapid construction of natural products featuring such motifs by using C2-symmetrical 1,3-bis(boronic esters). As for its application in convergent syntheses it was important to establish a selective mono-Zweifel olefination we describe the scope and limitations by using different 1,3-bis(boronic esters) and nucleophiles. This protocol takes advantage of the combination of the Hoppe–Matteson–Zweifel chemistry, which was elegantly put into practice by Aggarwal et al. In order to show its applicability the total syntheses of two natural products, serricornin and (+)-invictolide, were performed.
AB - anti-Configured 1,3-dimethyl deoxypropionate motifs are important sub structures in natural products. Herein, we describe a bidirectional approach for the rapid construction of natural products featuring such motifs by using C2-symmetrical 1,3-bis(boronic esters). As for its application in convergent syntheses it was important to establish a selective mono-Zweifel olefination we describe the scope and limitations by using different 1,3-bis(boronic esters) and nucleophiles. This protocol takes advantage of the combination of the Hoppe–Matteson–Zweifel chemistry, which was elegantly put into practice by Aggarwal et al. In order to show its applicability the total syntheses of two natural products, serricornin and (+)-invictolide, were performed.
KW - C-symmetry
KW - desymmetrization
KW - lithiation–borylation chemistry
KW - mono-Zweifel olefination
KW - natural product synthesis
UR - http://www.scopus.com/inward/record.url?scp=85085959989&partnerID=8YFLogxK
U2 - 10.1002/chem.202000599
DO - 10.1002/chem.202000599
M3 - Article
C2 - 32068298
AN - SCOPUS:85085959989
VL - 26
SP - 7998
EP - 8002
JO - Chemistry - a European journal
JF - Chemistry - a European journal
SN - 0947-6539
IS - 36
ER -