Melifoliox B, a novel phloroglucin derivative isolated from Melicope barbigera (Rutaceae) and synthesis of new oxidation products from melifoliones A and B

• Horst Weber,
• Kim-Thao Tran-Cong,
• Bernhard Mayer,
• Guido J. Reiss,
• Iryna S. Konovalova,
• Marc S. Appelhans,
• Kenneth R. Wood and
• Claus M. Passreiter

Beilstein J. Org. Chem. 2026, 22, 535–546, doi:10.3762/bjoc.22.39

• been described in the literature. Keywords: Melicope barbigera; Melifoliones A and B; new heterocyclic ring systems; new natural compounds; para-quinols; phenol oxidation; Introduction The genus Melicope is a member of the Rutaceae (Citrus family) and contains more than 200 species distributed in the

Bioinspired total syntheses of natural products: a personal adventure

• Zhengyi Qin,
• Yuting Yang,
• Nuran Yan,
• Xinyu Liang,
• Zhiyu Zhang,
• Yaxuan Duan,
• Huilin Li and
• Xuegong She

Beilstein J. Org. Chem. 2025, 21, 2048–2061, doi:10.3762/bjoc.21.160

• might undergo benzylic oxidations and intramolecular dehydration to access a diaryltetrahydrofuran (THF) skeleton. Then, oxidation of one aryl group through phenol oxidation would generate a putative cyclohexadienone intermediate to be further captured by the other phenol to access eupodienone through a

Copper catalysis with redox-active ligands

• Agnideep Das,
• Yufeng Ren,
• Cheriehan Hessin and
• Marine Desage-El Murr

Beilstein J. Org. Chem. 2020, 16, 858–870, doi:10.3762/bjoc.16.77

• could be circumvented through ligand modification. Phenol oxidation is ubiquitous in biological systems as demonstrated by the involvement of the copper enzymes tyrosinases (type III) in the melanogenesis process. The regioselectivity and reactivity of the oxidation of phenols are strongly dependent on

• metalloenzymatic active site was not characterized in detail, it might bear some resemblance to the original biological active site. Building on their previously discussed phenol oxidation methodology (Scheme 5 and Scheme 6), Lumb and co-workers have targeted subsequent C–N bond formation to access oxindoles [34

2-Iodo-N-isopropyl-5-methoxybenzamide as a highly reactive and environmentally benign catalyst for alcohol oxidation

• Takayuki Yakura,
• Tomoya Fujiwara,
• Akihiro Yamada and
• Hisanori Nambu

Beilstein J. Org. Chem. 2018, 14, 971–978, doi:10.3762/bjoc.14.82

• of the iodobenzamides depends on the ortho-relationship of the iodine atom to the amide group. Therefore, we then investigated N-isopropyl-2-iodobenzamides that have an additional functional group on the benzene ring. Based on the results of our studies on phenol oxidation [60][62] and Ishihara’s [52

New enzymatically polymerized copolymers from 4-tert-butylphenol and 4-ferrocenylphenol and their modification and inclusion complexes with β-cyclodextrin

• Adam Mondrzyk,
• Beate Mondrzik,
• Sabrina Gingter and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 2118–2123, doi:10.3762/bjoc.8.238

• potential. Other signals are poorly resolved (Figure 1B). In comparison, the CV measurements of 2 show anodic peak potentials of 0.66 and 0.90 V and cathodic peak potentials of 0.58 and 0.77 V. According to the literature, Fc-oxidation/reduction takes place at lower voltages than phenol oxidation/reduction

• [20]. The shift of peak potentials of polymerized 4-ferrocenylphenol in comparison to monomeric 4-ferrocenylphenol is +0.08 V for Fc oxidation/reduction and +0.19 V for phenol oxidation/reduction. In conclusion, phenol-moieties are oxidized preferably in copolymer 7, because the ferrocenyl moieties

• complex with adamantylcarboxylate (•••). Synthetic pathway to the desired polymer 7. Summary of peak potentials acquired by cyclic voltammetry (ferrocenyl oxidation or reduction/phenol oxidation or reduction). Supporting Information The Supporting Information features a copy of the ROESY NMR spectrum of