A mild procedure for hydrolysis of alkoxymethyl aryl ethers to give hydroxyarenes. A rational synthesis of ascofuranone

Highly Efficient and Selective Deprotection Method for Prenyl, Geranyl, and Phytyl Ethers and Esters Using Borontrifluoride–Etherate

“…Our literature survey revealed that several alkyl groups (methyl, [7][8][9][10] ethyl, [11] t-butyl [12,13] ) have been used to protect the phenolic compounds; however, they need drastic conditions for protection as well as deprotection, which also affect other functional groups. Newer protecting groups such as methoxymethylchloride (MOMCl) [14][15][16][17][18] methoxyethoxymethylchloride (MEMCl), [19] 2-(trimethylsilyl) ethoxymethylchoride (SEMCl), [20,21] and tetrahydrophyranoether (THP ethers) [22,23] have been developed that needs milder conditions. The prenyl group has also been used for protection of alcohols and phenols; [24][25][26][27][28][29][30][31][32][33][34] however, the reported reagents in deprotection of the prenyl group lack selectivity in multifunctional compounds.…”

Alternative oxidase inhibitors: Mitochondrion‐targeting as a strategy for new drugs against pathogenic parasites and fungi

“…Saimoto's attempts to reproduce Chen's procedure for the deprotection of Me‐ethers (ie, trimethylsilyl iodide in CHCl 3 /pyridine for 4 days) was not successful. Hence, an alternative using P 2 I 4 under neutral conditions was proposed to cleave the 1‐alkoxymethyl aryl ether under mild conditions (Scheme ) …”

“…The CpAOX genes encode a polypeptide of 336 amino acids having a predicted N-terminal targeting sequence similar to those found in proteins targeted to the mitochondria of other species. CpAOX was reported to be inhibited by AF (188) 6 and the potential of AOX as a novel target for chemotherapy against C. parvum was further corroborated by the inhibition of in vitro growth of C. parvum by SHAM (2) and 8-hydroxyquinoline (71). 6 An AOX has also been reported to be present in other intestinal parasites such as B. hominis, 2,[6][7][8]23 where it was thought that AOX helps Blastocystis cope with oxygen stress conditions in the intestine of the host and avoid the formation of reactive oxygen species (ROS).…”

“…After the groups of Kita, investigating the pharmacophore of AF (188), reported that the electron withdrawing cyano group was a useful alternative to its formyl group, 59 West et al 159,160 investigated the SAR of 3-chloro-4-hydroxybenzonitrile analogues. With the aim of reducing the lipophilicity of the tail region of inhibitor 200, and thereby improve its physicochemical properties including the predicted CNS multiparameter optimization score, 161 they introduced different polar groups (amide and ether) in the lipophilic tail ( Figure 15).…”

Sigmatropic Rearrangements and Related Processes Promoted by Silver

“…For example, DDQ oxidation of the appropriate dihydro-3(2H)-furanone enol acetates (Table 3.5, entries 1 and 7) afforded bullatenone and the antitumor agent geiparvarin in a very rapid route (Fig. 71 More [3,3]-SIGMATROPIC REARRANGEMENTS importantly, chirality transfer was studied and showed to be quantitative, indicating that cyclization was more rapid than isomerization of the allene intermediate. 69,70 Toward the total synthesis of (À)-ascofuranone (Scheme 3.45), an antibiotic with hypolipidemic, antihypertensive, and antitumor properties, several improvements have been made.…”