Utiziling a copper-free Sonogashira reaction in the synthesis of the leukotriene a4 hydrolase modulator batatasin IV was written by Petruncio, Greg;Girgis, Michael;Moummi, Sanae;Jayatilake, Meth;Lee, Kyung Hyeon;Paige, Mikell. And the article was included in Tetrahedron Letters in 2020.Synthetic Route of C8H8O3 This article mentions the following:
Batatasin IV is a dihydrostilbenoid isolated from Chinese yams which was shown to have inhibitory activities against plant growth. Later studies showed that this compound may exhibit anti-inflammatory properties by inhibiting the epoxide hydrolase activity of the leukotriene A4 hydrolase enzyme. To access the dihydrostilbenoid skeleton, a copper-free SPhos-mediated Sonogashira reaction was conceived and the substrate scope was explored. Our results indicate that the reaction can tolerate the presence of free alcs., aldehydes, nitro groups, and anilinyl groups. However, a substituent with an acidic phenol or carboxylic acid group gave significantly lower yields. Next, a total synthesis of batatasin IV was accomplished in 16% overall yield incorporating the reported copper-free Sonogashira reaction. Finally, we show that batatasin IV inhibits the hydrolysis of alanine p-nitroanilide by leukotriene A4 hydrolase with an IC50 of 91.4娓璏. In the experiment, the researchers used many compounds, for example, 3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8Synthetic Route of C8H8O3).
3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Synthetic Route of C8H8O3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem