A sequential asymmetric conjugate addition/cyclisation of α-bromohydroxamates with -quinone methide derivatives has been developed, which provides enantioenriched 1,4-benzoxazepines in generally high yields (up to 95%) and good enantioselectivities (up to 97 : 3 er). This protocol not only offers a novel and straightforward strategy for constructing chiral 1,4-benzoxazepines, but also demonstrates the potential of α-bromohydroxamates as three-atom synthons in asymmetric cyclisation reactions.
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http://dx.doi.org/10.1039/d3cc02368k | DOI Listing |
Bioorg Chem
December 2024
School of Marine Sciences, Sun Yat-sen University, Guangdong Provincial Key Laboratory of Marine Resources and Coastal Engineering, Pearl River Estuary Marine Ecosystem Research Station, Ministry of Education, Southern Laboratory of Ocean Science and Engineering (Guangdong, Zhuhai), Zhuhai 519000, China. Electronic address:
J Am Chem Soc
December 2024
State Key Laboratory of Organometallic Chemistry and Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS 345 Lingling Road, Shanghai 200032, P. R. China.
Here, we report a novel strategy for the preparation of diverse heterocycles via a Pd-catalyzed migratory 1,1-cycloannulation reaction (MCAR) of alkenes. Starting from readily available alkenyl amines and alkenyl alcohols, this approach allows the formation of a wide range of five- to seven-membered azaheterocycles and oxaheterocycles with high efficiency and good functional group tolerance. The key to the realization of this reaction is the use of 4-iodophenol or 2-iodophenol derivatives where the phenolic hydroxyl group plays a critical role in controlling the direction of migration and the ring-size of the heterocycles through the formation of a quinone methide intermediate.
View Article and Find Full Text PDFJ Pharm Biomed Anal
December 2024
Department of Natural Medicine and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, PR China. Electronic address:
Higenamine (HG), a naturally occurring benzyltetrahydroisoquinoline alkaloid, has been revealed a variety of biological activities and is extensively utilized in dietary supplements. Currently, HG is under investigation in phase I clinical trials, however, the liver metabolism of HG has so far not been fully elucidated. The present study aimed to identify reactive metabolites of HG using ultrahigh-performance liquid chromatography-tandem mass spectrometry.
View Article and Find Full Text PDFBiomacromolecules
December 2024
Department of Bionanotechnology and Bioconvergence Engineering, Jeonbuk National University, Jeonju, Jeonbuk 54896, Korea.
Org Lett
December 2024
Institut für Pharmazeutische Biologie und Biotechnologie, Fachbereich Pharmazie, Philipps-Universität Marburg, Robert-Koch-Straße 4, 35037Marburg, Germany.
Genome mining and gene deletion experiments in proved the involvement of the PKS-NRPS PemA and the -enoyl reductase PemB in the formation of three enantiomeric clavatol-containing tetramate pairs. Overexpression of a transcription factor significantly improved the product yields. Feeding experiments provided evidence for their formation via 1,4-Michael addition of hydroxyclavatol to two tetramates from the Pem pathway.
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