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 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.
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.
