A substrate-induced stereocontrol strategy was used to gain access to the tetracyclic core of (-)-lemonomycin. An advanced intermediate was prepared from a known substituted tyrosinol through a 16-step sequence, which involved a Pictet-Spengler reaction, a [3+2] dipolar cycloaddition and an enamide hydrogenation.
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http://dx.doi.org/10.1016/j.tet.2013.05.009 | DOI Listing |
Org 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 PDFJ Org Chem
January 2025
Chang-Kung Chuang Institute, Shanghai Frontiers Science Center of Molecule Intelligent Syntheses, College of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.
A new stereoselective [4+2] annulation method for constructing tetracyclic indolines by reacting indoles with bicyclic N-substituted cyclobutanes has been developed. Using Sc(OTf) as a catalyst, a series of tetracyclic indolines with four continued stereogenic carbon centers have been obtained in ≤86% yields as single diastereomers. This reaction offers an accessible way for the rapid construction of the core structures of biologically active natural products like paucidirinine, deethylibophyllidine, and ibophyllidine.
View Article and Find Full Text PDFActa Crystallogr E Crystallogr Commun
January 2025
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan.
The title compounds, CHO ( and ), are tetra-cyclic benzoates composed of a taxane ring with a fused dioxolane ring as the core skeleton. In compound , the five-membered dioxolane ring is essentially planar while the two cyclo-hexane rings and the cyclo-octane ring adopt chair and chair-chair forms, respectively, and there are three intra-molecular H⋯H short contacts. The corresponding ring conformations in are similar; however, one intra-molecular C-H⋯O inter-action and two H⋯H short contacts are observed, and the benzoyl and meth-oxy-methyl groups show orientational disorder.
View Article and Find Full Text PDFOrg Lett
January 2025
Key Laboratory of Chemical Biology (Ministry of Education), Shandong Basic Science Research Center (Pharmacy), School of Pharmaceutical Sciences, Shandong University, Jinan, Shandong 250012, China.
Metabolic blockade-based genome mining of the marine sediment-derived SCSIO 07745 led to the discovery of 11 novel aminoquinolinone alkaloids, oxazoquinolinones A-J (-), characterized by an oxazolidone[3,2-α]quinoline-5,8-dione scaffold, and oxazoquinolinone K (), featuring an unprecedented fused 6/6/6/5 tetracyclic core ring system. Additionally, 5 new biosynthetic intermediates or shunt products (-) and a known metabolite sannanine () were identified. Their structures were elucidated by extensive spectroscopic analyses and a comparison of electronic circular dichroism and single-crystal X-ray diffraction.
View Article and Find Full Text PDFSynthesis (Stuttg)
January 2024
Department of Chemistry, Purdue University, 720 Clinic Drive, West Lafayette, Indiana 47907, USA.
alkaloid complanadine A, isolated by Kobayashi et al. in 2000, is a complex and unsymmetrical dimer of lycodine. Biologically, it is a novel and promising lead compound for the development of new treatment for neurodegenerative disorders and persistent pain management.
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