A new synthetic route to D-trishomocubanone and oxa- D-trishomocubane derivatives has been established by the rearrangement approach. A remotely located methyl substituent in the six-membered ring contributed to the acid-catalyzed rearrangement of the cage dione in an unusual fashion. This rearrangement approach provided an attractive route to extended D-trishomocubanes, which are not accessible by the conventional multistep synthetic sequence. For the first time, two phenyl groups were incorporated from the solvent into the strained trishomocubane skeleton in an unprecedented manner via carbocation-mediated rearrangement with the aid of BF·OEt. Interestingly, an oxa-bridged trishomocubane skeleton was also formed during acid-promoted rearrangement.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.8b00449 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Discovery of WDR5-MLL1 and HDAC Dual-Target Inhibitors for the Treatment of Acute Myeloid Leukemia.
J Med Chem
January 2025
Jiangsu Key Laboratory of Drug Design and Optimization and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, China.
Targeting the WDR5-MLL1 protein-protein interaction (PPI) is considered to be an effective approach for the treatment of MLL-rearranged leukemia. However, interfering with WDR5-MLL1 PPI reduces methylated H3K4 levels and induces a decline in acetylated H3 levels, which may contribute to the suboptimal cellular efficacy of WDR5 inhibitors. We observed that cotreatment with WDR5-MLL1 PPI and HDAC inhibitors augmented the antiproliferative effect in MV-4-11 cells.
View Article and Find Full Text PDFDiscovery and Total Synthesis of a New Class of Minor Immunosuppressive Plant Sesterterpenoids.
Angew Chem Int Ed Engl
January 2025
Kunming Institute of Botany Chinese Academy of Sciences, State Key Laboratory of Phytochemistry and Plant Resources in West China, Lanhei Road 132, Heilongtan, 650201, Kunming, CHINA.
Plant sesterterpenoids are an extremely rare family of natural products that generally possess novel chemical structures and diverse biological activities. Here, we report the discovery of an unprecedented group of minor plant sesterterpenoids, gracilisoids B-E (2-5), which feature two types of highly functionalized bicyclo[3.2.
View Article and Find Full Text PDFCryptochrome magnetoreception: Time course of photoactivation from non-equilibrium coarse-grained molecular dynamics.
Comput Struct Biotechnol J
December 2024
Department of Physics, University of Exeter, Stocker Rd., Exeter EX4 4QL, UK.
Magnetoreception, the ability to sense magnetic fields, is widespread in animals but remains poorly understood. The leading model links this ability in migratory birds to the photo-activation of the protein cryptochrome. Magnetic information is thought to induce structural changes in cryptochrome via a transient radical pair intermediate.
View Article and Find Full Text PDFQuantification of 3D microstructures in Achilles tendons during in situ loading reveals anisotropic fiber response.
Acta Biomater
January 2025
Department of Biomedical Engineering, Lund University, Box 118, 221 00 Lund, Sweden.
While the number of studies investigating Achilles tendon pathologies has grown exponentially, more research is needed to gain a better understanding of the complex relation between its hierarchical structure, mechanical response, and failure. At the microscale, collagen fibers are, with some degree of dispersion, primarily aligned along the principal loading direction. However, during tension, rearrangements and reorientations of these fibers are believed to occur.
View Article and Find Full Text PDFMolecular mechanism underlying the modulation of typical properties of starch by Quillaja saponins: Multi-experimental evidence and two-stage MD simulation.
Int J Biol Macromol
January 2025
College of Biosystems Engineering and Food Science, Key Laboratory for Quality Evaluation and Health Benefit of Agro-Products of Ministry of Agriculture and Rural Affairs, Key Laboratory for Quality and Safety Risk Assessment of Agro-Products Storage and Preservation of Ministry of Agriculture and Rural Affairs, Zhejiang University, Hangzhou 310058, China. Electronic address:
Quillaja saponins (QS), a natural amphiphilic food additive, have significant potential in modulating the properties of starchy products. However, a systematic understanding of this phenomenon and the underlying molecular mechanisms remains lacking. In this study, two-stage molecular dynamics (MD) simulations combined with multiple experimental approaches were employed to investigate the modulation of starch properties by QS through six chain dynamic behaviors.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!