89461-52-9Relevant academic research and scientific papers
A PRACTICAL METHOD FOR MULTIGRAM SCALE SYNTHESIS OF (+)-METHYL 5(S),6(R)-EPOXY-6-FORMYLHEXANOATE AND 2(R),3(S)-EPOXYOCTANAL, KEY INTERMEDIATES FOR SYNTHESIS OF LEUKOTRIENES A4
Kobayashi, Yuichi,Kitano, Yasunori,Matsumoto, Takashi,Sato, Fumie
, p. 4775 - 4778 (1986)
A practical method for multigram scale synthesis of (+)-methyl 5(S),6(R)-epoxy-6-formylhexanoate (1) and 2(R),3(S)-epoxyoctanal (13), key intermediates for synthesis of leukotrienes A4, starting with (R)-glyceraldehyde acetonide (3) is described.
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 (2015/08/18)
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
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.
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.
Total synthesis of leukotrienes from butadiene
Rodriguez, Ana,Nomen, Miguel,Spur, Bernd W.,Godfroid, Jean-Jacques,Lee, Tak H.
, p. 2991 - 3000 (2007/10/03)
The total synthesis of leukotrienes has been achieved starting from butadiene by a palladium-catalyzed telomerization at room temperature. A Sharpless catalytic asymmetric epoxidation generated the asymmetric centers with >94% ee. Simple transformations of the key intermediate 15 produced the leukotrienes LTA4 methyl ester (4), LTC4 (1), LTD4 (2) and LTE4 (3), as well as (14S, 15S)-LTA4 methyl ester (24) and the novel [2H2]-LTA4 methyl ester (28). The use of the opposite chiral director in the Sharpless catalytic asymmetric epoxidation gave the key intermediate 15a that has been used in the synthesis of the double epimers of the leukotrienes as well as LTB4.
A highly efficient practical method for the synthesis of chiral polyhydroxy-(E,E)-1-chlorodienols and (E)-5-hydroxy enynes
Yadav,Barma,Dutta, Dinah
, p. 4479 - 4482 (2007/10/03)
An efficient protocol for the synthesis of chiral polyhydroxy-(E, E)-1-chlorodienols and (E)-5-hydroxy enynes from chiral 4,5-epoxy trans allyl chlorides and 4,5-O-isopropylidene allyl chlorides is described by using stoichiometric amount of LiNH2 or LDA in HMPA : THF (1 : 5) useful in the synthesis of biologically active natural products.
Titanocene induced deoxygenation of di-epoxides - A convenient regioselective preparation of 1,3-diols
Yadav,Srinivas, Dale
, p. 905 - 906 (2007/10/03)
Titanocene induced regioselective opening of 2,4-di-epoxy alcohols to 1-ene-3,5-diols is described. Diepoxy alcohols were treated with 3 eq. of Cp2TiCl in dry THF to obtain 1-ene-3,5 diols with conservation of stereochemistry at C-3 and C-5 was
SYNTHESIS OF 5S-HYDROXY-14,15 LTA4 A BIOGENIC PRECURSOR TO THE LIPOXINS
Leblanc, Yves,Fitzsimmons, Brian J.,Rokach, Joshua
, p. 3449 - 3452 (2007/10/02)
A synthesis of 5S-hydroxy-14,15-LTA4 10 an intermediate in the biosynthesis of the lipoxins is described.
THE STEREOSPECIFIC SYNTHESIS OF 14S,15S-OXIDO 5Z,8Z,10E,12E-EICOSATETRAENOIC ACID
Zamboni, Robert,Milette, Suzanne,Rokach, Joshua
, p. 4899 - 4902 (2007/10/02)
The first total and stereospecific synthesis of 14S,15S-oxido 5Z,8Z,10E,12E-eicosatetraenoic acid from 2-deoxy-D-ribose has been achieved.
