Synonyms:eleutherobin
≥98% （HPLC） *data from raw suppliers
ELEUTHEROBIN 95.00% *data from reagent suppliers
There total 57 articles about Eleutherobin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
Reference yield: 96.0%
Reference yield: 91.0%
Reference yield: 60.0%
The study focuses on the synthesis and evaluation of a glycopeptide inhibitor of E-selectin, a receptor involved in cell adhesion processes during inflammation and metastasis of tumor cells. The researchers aimed to create a stable, enzymatically resistant ligand that mimics the sialyl Lewis* structure, which is a natural ligand for E-selectin. To achieve this, they used a β-D-arabinopyranoside as a substitute for the α-L-fucoside in the sialyl Lewis* structure, hypothesizing that the arabinose would be more resistant to enzymatic degradation due to its absence in mammals. Key chemicals used in the study include ethylthio-2,3,4-tri-O-benzyl-α,β-D-arabinopyranoside, N-iodosuccinimide (NIS), trifluoromethane sulfonic acid (TfOH), Raney nickel, Fmoc-protected amino acids, and various other reagents for peptide synthesis. These chemicals served the purpose of constructing the synthetic E-selectin ligand, which was then tested for its ability to inhibit the adhesion of cells to E-selectin, demonstrating a significant increase in affinity compared to natural ligands.
The research presents a formal total synthesis of eleutherobin, a natural product with antitumor activity. The key step of the strategy involves a ring-closing metathesis (RCM) reaction of a densely functionalized diene. The study investigates the unusual kinetically controlled RCM stereochemistry using computational methods. The synthesis begins with the preparation of aldehyde 6 from R-(–)-carvone through a series of reactions, which is then converted into diene 5 via stereoselective titanium-mediated Hafner–Duthaler oxyallylation reactions. The RCM reaction of diene 5 using Grubbs' second-generation catalyst leads to the formation of the ten-membered carbocycle (E)-14, which is less thermodynamically stable but formed under kinetic control. Further transformations including removal of protective groups and oxidation lead to the key intermediate 3, which is identical to the data reported by Danishefsky and co-workers. The research also explores the stereochemical outcome of the RCM reaction and the subsequent isomerization of the enedione using molecular mechanics, semiempirical PM3 calculations, and density functional theory (DFT) calculations. The study highlights the role of the p-methoxyphenyl (PMP) protective group in facilitating the RCM reaction and the formation of the kinetically controlled E isomer.
The research focuses on the synthesis of N-methyl urocanates of hydroxy derivatives of isocembrol, which are proposed biomimetics of taxol and exhibit cytotoxic activity similar to eleutherobin and sarcodictyins. The experiments involved stereospecific hydroxylation of isocembrol to prepare alcohols, which were then esterified into N-methylurocanates. Key reactants included isocembrol, t-butylhydroperoxide (TBHP), VO(acac)2, LiAlH4, (i-Bu)2AlH, SeO2, and N-methylurocanic acid, among others. The analyses used to characterize the products and intermediates were primarily nuclear magnetic resonance (NMR) spectroscopy, including both proton (PMR) and carbon (13C NMR) variants, as well as thin-layer chromatography (TLC), optical rotation measurements, and melting point determinations. These techniques were crucial in establishing the regio- and stereochemistry of the synthesized compounds.
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