Total Synthesis and Cytotoxic Activity of 7-O-Methylnigrosporolide and Pestalotioprolide D was written by Thiraporn, Aticha;Iawsipo, Panata;Tadpetch, Kwanruthai. And the article was included in Synlett in 2022.Recommanded Product: 105-13-5 This article mentions the following:
A convergent total synthesis of 7- O-methylnigrosporolide and pestalotioprolide D has been accomplished in 17 linear steps and overall yields of 1.7% and 2.6%, resp., starting from ( S)-propylene oxide and ( S)-benzyl glycidyl ether. Our synthesis exploited an acetylide addition and a Shiina macrolactonization to assemble the macrocycle, a Lindlar reduction, and Wittig and Still-Gennari olefinations to construct the three alkene groups, as well as a Jacobsen hydrolytic kinetic resolution to install the stereogenic center. The selection of the silyl protecting group of the C-4 alc. was crucial for the final deprotection step. Our synthesis also led to a hypothesis that pestalotioprolide D might be an artifact of 7- O-methylnigrosporolide. The cytotoxic activities of the two synthetic compounds against six human cancer cell lines were evaluated. Synthetic pestalotioprolide D showed more potent cytotoxic activity than 7-O-methylnigrosporolide against all the cancer cell lines tested, and the SiHa cervical cancer cell line was the most sensitive to both synthetic compounds In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Recommanded Product: 105-13-5).
(4-Methoxyphenyl)methanol (cas: 105-13-5) 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. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Recommanded Product: 105-13-5
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem