73957-99-0Relevant articles and documents
Synthesis of epoxyisoprostanes: Effects in reducing secretion of pro-inflammatory cytokines IL-6 and IL-12
Egger, Julian,Bretscher, Peter,Freigang, Stefan,Kopf, Manfred,Carreira, Erick M.
, p. 5382 - 5385 (2013/06/26)
Anti-inflammatory: The efficient and general synthetic route to the elusive epoxyisoprostanoid phospholipids PECPC and PEIPC, along with the isoprostanoids EC and EI, relies on a number of stereo- and chemoselective steps, including a C-H insertion for the rapid construction of the cyclopentanone ring. The synthesized compounds display unprecedented biological activity in reducing the secretion of pro-inflammatory cytokines. Copyright
Total Synthesis and Determination of the Absolute Configuration of Frondosin B
Masayuki, Inoue,Carson, Mattew W.,Frontier, Alison J.,Danishefsky, Samuel J.
, p. 1878 - 1889 (2007/10/03)
Two concise syntheses of (+/-)-frondosin B (1), an interleukin-8 receptor antagonist, have been achieved from commercially available 5-methoxysalicylaldehyde. The seven-membered ring in ketone 33, the common intermediate for both syntheses, was built by a
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.
Total synthesis of lipoxin A4 and lipoxin B4 from butadiene
Rodríguez,Nomen,Spur,Godfroid,Lee
, p. 823 - 826 (2007/10/03)
The total synthesis of LXA4 and LXB4 has been achieved starting from butadiene via palladium catalyzed telomerization. Sharpless catalytic AE and C-2 inversion of the 2(S),3(S)-epoxy alcohols, using Myers CO2/Cs2CO3 procedure, generated the asymmetric centers. The flexibility of the strategy allows an easy access to the linear eicosanoids. (C) 2000 Elsevier Science Ltd.
A PRACTICAL METHOD FOR THE PRODUCTION OF METHYL 5(S)-BENZOYLOXY-5-FORMYLPENTANOATE - A KEY INTERMEDIATE IN THE SYNTHESIS OF LEUKOTRIENE B4
Kornilov, A. M.,Furmanova, M. V.,Sorochinskii, A. E.,Kukhar', V. P.
, p. 1067 - 1069 (2007/10/02)
Catalytic epoxidation of methyl 7-hydroxy-5(E)-heptenoate by the Sharpless method gave optically pure (5R,6R)-methyl 5,6-epoxy-7-hydroxyheptanoate, in which regioselective opening of the epoxide ring by benzoic acid with the assistance of titanium tetrais
Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. Part 39. Enantioselective Synthesis of 1,3-Dioxin-4-ones Having 2,3-Dihydroxy- or 2,3,4-Trihydroxyalkyl Groups at the 6-Position: Versatile Building Blocks of Polyhydroxylated 4-7 Carbon Backbones
Sugita, Yoshiaki,Sakaki, Jun-ichi,Sato, Masayuki,Kaneko, Chikara
, p. 2855 - 2862 (2007/10/02)
1,3-Dioxin-4-ones having 3-hydroxyprop-1-enyl and 2-hydroxybut-3-enyl groups at the 6-position afford, after the Sharpless asymmetric epoxidation followed by epoxide ring cleavage, the 6-- and 6-dioxinones.The former acts as a four- and six-carbon building block, while the latter as a five- and seven-carbon building block.
SYNTHESES OF PROSTAGLANDIN AND LEUKOTRIENE C7 SYNTHONS THROUGH COMMON INTERMEDIATE COMPOUNDS
Bobrova, N. I.,Belosludtsev, Yu. Yu.,Pivnitskii, K. K.
, p. 1873 - 1878 (2007/10/02)
A method is proposed for the production of the C7-synthons used in the synthesis of eicosanoids (the methyl esters of 7-hydroxy-5Z-heptenoic and 6-formyl-5,6-trans-epoxyhexanoic acids) by a common scheme from readily obtainable tetrahydrofuran and propargyl alcohol.
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 (2007/10/02)
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.
