Details
| Original language | English |
|---|---|
| Pages (from-to) | 1615-1619 |
| Number of pages | 5 |
| Journal | Chemistry - a European journal |
| Volume | 27 |
| Issue number | 5 |
| Early online date | 20 Nov 2020 |
| Publication status | Published - 21 Jan 2021 |
Abstract
The first total synthesis of halioxepine is accomplished using a 1,4-addition for constructing the quaternary center at C10 and a halo etherification for the generation of the tertiary ether at C7. The correct structure of halioxepine was determined by assembling different enantiomeric building blocks and by changing the relative configuration between C10 and C15.
Keywords
- halo etherification, natural product synthesis, quaternary stereocenter, structure elucidation, terpenoids
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Chemistry - a European journal, Vol. 27, No. 5, 21.01.2021, p. 1615-1619.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Total Synthesis and Structure Revision of Halioxepine
AU - Poock, Caroline
AU - Kalesse, Markus
N1 - Funding Information: We are very grateful to Prof. J. Tanaka (University of the Ryukyus) for providing NMR-Spectra of authentic halioxepine. We also thank Prof. J. Rodriguez (Universidade da Coru?a) for cooperation with respect to NMR-spectra. We thank Dr. J. Fohrer, M. Rettstadt and D. K?rtje for detailed NMR analysis and A. Schulz and R. Reichel for mass spectra. In terms of preparation of the manuscript we thank Alina Eggert, Giada Tedesco, Alexandru-Adrian Sara and Daniel L?cke. Open access funding enabled and organized by Projekt DEAL.
PY - 2021/1/21
Y1 - 2021/1/21
N2 - The first total synthesis of halioxepine is accomplished using a 1,4-addition for constructing the quaternary center at C10 and a halo etherification for the generation of the tertiary ether at C7. The correct structure of halioxepine was determined by assembling different enantiomeric building blocks and by changing the relative configuration between C10 and C15.
AB - The first total synthesis of halioxepine is accomplished using a 1,4-addition for constructing the quaternary center at C10 and a halo etherification for the generation of the tertiary ether at C7. The correct structure of halioxepine was determined by assembling different enantiomeric building blocks and by changing the relative configuration between C10 and C15.
KW - halo etherification
KW - natural product synthesis
KW - quaternary stereocenter
KW - structure elucidation
KW - terpenoids
UR - http://www.scopus.com/inward/record.url?scp=85097881614&partnerID=8YFLogxK
U2 - 10.1002/chem.202004847
DO - 10.1002/chem.202004847
M3 - Article
C2 - 33215739
AN - SCOPUS:85097881614
VL - 27
SP - 1615
EP - 1619
JO - Chemistry - a European journal
JF - Chemistry - a European journal
SN - 0947-6539
IS - 5
ER -