89461-52-9Relevant articles and documents
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.
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.
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.
