A simple and straightforward synthetic approach to potential anti-infective thiolactone-isatin hybrids led to the discovery of novel tetracyclic compounds which bear a macrocylic motif containing an unusual bridged amide bond.
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http://dx.doi.org/10.3762/bjoc.6.78 | DOI Listing |
J Org Chem
January 2025
School of Medicine, Shanghai University, 99 Shangda Road, BaoShan District, Shanghai 200444, China.
Uncommon diterpenoids with diverse frameworks, including one unexpected iodinated oxa-6/6/6/6-tetracyclic diterpene () and its monobrominated 6/6/6-tricyclic analogue () and one novel isodolastane-type diterpene featuring an unusual aromatic 5/7/6-tricyclic ring system () as well as a related known dolastane-type diterpenoid (), were isolated from the South China Sea sponge . Their structures, including absolute configurations, were established by extensive spectroscopic data analysis, X-ray diffraction analysis, and quantum mechanical-nuclear magnetic resonance and time-dependent density functional theory/electronic circular dichroism calculations. A plausible biosynthetic pathway of new compounds - was proposed.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, China.
(±)-Melichuniiones A and B (1 and 2), two novel enantiomeric pairs of lignan-phloroglucinol hybrids with an unprecedented beadlike core were isolated from the leaves of , together with new analogues 3-6. Compounds 1 and 2 possess a unique dispiro [furan-2,5'-cyclopenta[]furan-2',3''-furan] 5/5/5/5 tetracyclic skeleton. Their structures were established by extensive spectroscopic analyses, single crystal X-ray diffraction, and electronic circular dichroism (ECD) calculations.
View Article and Find Full Text PDFMolecules
December 2024
Institut für Pharmazeutische und Medizinische Chemie, Universität Münster, Corrensstraße 48, D-48149 Münster, Germany.
J Org Chem
January 2025
College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, People's Republic of China.
A copper-catalyzed domino addition/cyclization reaction was developed to synthesize novel benzoselenazole-linked 1,2,3-triazole and tetracyclic fused 12-benzo[4,5]selenazole[2,3-]quinazolin-12-one derivatives from isoselenocyanates. This domino reaction efficiently constructed multiple new chemical bonds in a single step, forming either four (one C-Se and three C-) or three (one C-Se and two C-) bonds. The reaction offers several key advantages, including mild conditions, broad substrate compatibility, and straightforward and safe operation.
View Article and Find Full Text PDFSci Rep
January 2025
Centre for Molecular and Materials Science, TRIUMF, 4004 Wesbrook Mall, Vancouver, BC, V6T 2A3, Canada.
This paper describes muon spin spectroscopy studies of 12-phosphatetraphene stabilized by a peri-trifluoromethyl group and a meso-aryl substituent. Even though the prepared solution in tetrahydrofuran (THF) was quite dilute (0.060 M) for transverse-field muon spin rotation (TF-µSR) measurements, the π-extended heavier congener of tetraphene presented a pair of signals due to a muoniated radical from which the muon hyperfine coupling constant (hfc) was determined.
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