110222-66-7Relevant academic research and scientific papers
Mammalian blood odorant and chirality: synthesis and sensory evaluation by humans and mice of the racemate and enantiomers of trans-4,5-epoxy-(E)-2-decenal
Mori, Kenji,Osada, Kazumi,Amaike, Masayasu
, p. 861 - 867 (2015)
Abstract The racemate and enantiomers of trans-4,5-epoxy-(E)-2-decenal 1, an odorant with a metallic blood smell, were synthesized. The detection threshold for humans was 0.019 ppb for (2E,4S,5S)-(-)-1 and 0.62 ppb for (2E,4R,5R)-(+)-1, respectively. The
Discovery of a highly potent anti-inflammatory epoxyisoprostane-derived lactone
Egger, Julian,Bretscher, Peter,Freigang, Stefan,Kopf, Manfred,Carreira, Erick M.
supporting information, p. 17382 - 17385 (2015/02/19)
Epoxyisoprostanes EI (1) and EC (2) are effective inhibitors of the secretion of proinflammatory cytokines IL-6 and IL-12. In detailed studies toward the investigation of the molecular mode of action of these structures, a highly potent lactone (3) derived from 1 was identified. The known isoprostanoids 1 and 2 are most likely precursors of 3, the product of facile intramolecular reaction between the epoxide with the carboxylic acid in 2.
Synthesis of the four stereoisomers of 2,3-epoxy-4-hydroxynonanal and their reactivity with deoxyguanosine
Petrova, Katya V.,Stec, Donald F.,Voehler, Markus,Rizzo, Carmelo J.
supporting information; experimental part, p. 1960 - 1971 (2011/04/22)
2,3-Epoxy-4-hydroxynonanal (EHN) is a potential product of lipid peroxidation that gives rise to genotoxic etheno adducts. We have synthesized all four stereoisomers of EHN and individually reacted them with 2′-deoxyguanosine. In addition to 1,N2-etheno-2′- deoxyguanosine, 12 stereoisomeric products were isolated and characterized by 1H NMR and circular dichroism spectroscopy. The stereochemical assignments were consistent with selective NOE spectra, vicinal coupling constants, and molecular mechanics calculations. Reversed-phase HPLC conditions were developed that could separate most of the adduct mixture.
An organocatalytic approach to 2-hydroxyalkyl- and 2-aminoalkyl furanes
Albrecht, Lukasz,Ransborg, Lars Krogager,Gschwend, Bjoern,Jorgensen, Karl Anker
supporting information; experimental part, p. 17886 - 17893 (2011/02/23)
The first enantioselective methodology for the synthesis of electron-poor 2-hydroxyalkyl- and 2-aminoalkyl furanes is demonstrated in this study. It utilizes a highly stereoselective organocatalytic one-pot reaction cascade: epoxidation or aziridination o
Catalytic asymmetric epoxidation of α-branched enals
Lifchits, Olga,Reisinger, Corinna M.,List, Benjamin
supporting information; experimental part, p. 10227 - 10229 (2010/09/06)
An asymmetric catalytic epoxidation of α-branched, α,β-unsaturated aldehydes is presented. A highly synergistic combination of a primary cinchona-based amine and a chiral phosphoric acid was found to promote the reaction with excellent enantiocontrol for α-monosubstituted and α,β-disubstituted enals.
Synthesis of 14,15-epoxyisoprostane A2 phosphorylcholine
Acharya, Hukum P.,Miyoshi, Kei,Takashima, Yuji,Ogawa, Narihito,Kobayashi, Yuichi
body text, p. 1181 - 1189 (2009/07/05)
The product of the copper-promoted allylic substitution of the 4-hydroxycyclopent-2-enyl ester with TMS-C{triple bond, long}CCH2MgBr was converted to the cyclopentenone with the PMBO(CH2)4CH{double bond, long}CHCH2 side ch
Synthesis of β-dimorphecolic acid exploiting highly stereoselective reduction of a side-chain carbonyl group in a π-allyltricarbonyliron lactone complex
Ley, Steven V.,Meek, Graham
, p. 1125 - 1133 (2007/10/03)
A highly enantioselective synthesis of β-dimorphecolic acid 1 is reported. The synthesis features a diastereoselective reduction of the ketone 4, in which the tricarbonyliron lactone tether induces a 1,5 transfer of chirality, followed by a stereoselectiv
1,5-Asymmetric induction of chirality: Highly diastereoselective synthesis of homoallylic tertiary alcohols by the Lewis acid-mediated addition of allylstannanes into ketones in the side-chain of π-allyltricarbonyliron lactone complexes
Ley, Steven V.,Cox, Liam R.
, p. 3315 - 3325 (2007/10/03)
Allylstannanes add into ketone groups in the side-chain of π-allyltricarbonyliron lactone complexes to afford the corresponding homoallylic tertiary alcohol complexes with very high levels of diastereocontrol. The reaction provides an example of 1,5-asymmetric induction of chirality with the lactone tether acting as the source of induction. The endo addition complexes can be converted into (E,E)-dienes bearing an α tertiary alcohol chiral centre in two steps proceeding via the η4-dienetricarbonyliron complexes. No loss of enantio- or diastereo-purity is observed during decomplexation.
Synthesis of β-dimorphecolic acid exploiting highly stereoselective-reduction of a side-chain carbonyl group in a π-allyltricarbonyliron lactone complex
Ley,Meek
, p. 1751 - 1752 (2007/10/02)
A highly stereoselective synthesis of β-dimorphecolic acid is accomplished utilising a π-allyltricarbonyliron lactone complex 3 to control the formation of all the stereochemical features of the natural product.
ENANTIOSELECTIVE SYNTHESIS OF 1-VINYL-1,2-DIOLS, VINYL EPOXIDES AND α,β-DIALKOXY ALDEHYDES
Matsumoto, Takashi,Kitano, Yasunori,Sato, Fumie
, p. 5685 - 5688 (2007/10/02)
A practical synthetic method of chiral γ-trimethylsilylmethyl allylic alcohols (1) with both E- and Z-configuration has been developed.The alcohols 1 are readily converted into 1-vinyl-1,2-diols (5) via diastereoselective epoxidation followed by the react
