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The pentacyclic framework associated with the alkaloid (-)-lycorine (1) can be assembled in as few as six steps from the enantiomerically pure cis-1,2-dihydrocatechol 3 which is itself readily available on a large scale through the whole-cell biotransformation of bromobenzene. The methodology has been used in developing the first synthesis of compound 2, a derivative of lycorine.
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http://dx.doi.org/10.1021/ol901364n | DOI Listing |
ACS Cent Sci
August 2025
Hefei National Research Center of Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.
Asymmetric organo-metal combined catalysis, which integrates the catalytic functions of chiral organocatalysts and metal complexes, enables the enantioselective formation of challenging chemical bonds and facilitates cascade transformations, often without the need for intermediate purification. Since its inception in 2001, this paradigm has evolved into a versatile strategy for the rapid construction of molecular complexity with a high level of enantioselectivity. In this Outlook, we have highlighted the most recent contributions to this field, showcasing exciting opportunities to overcome current efficiency limits.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
August 2025
State Key Laboratory of Green Pesticide; Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Huaxi District, Guiyang, 550025, China.
In contrast to the notable advancements focusing on the preparation of optically enriched S(IV) frameworks in recent years, achieving catalyst stereocontrol over S(VI) stereogenicity to generate chiral S(VI) scaffolds remains a largely underexplored challenge. Herein, we document a new activation mode of isothiourea organocatalysis for the highly enantioselective synthesis of S(VI)-chiral sulfonimidates. This method involves the covalent activation of racemic S(VI) sulfonimidoyl chlorides through the formation of a pivotal isothiourea-bound sulfonimidoyl intermediate.
View Article and Find Full Text PDFAnal Chem
September 2025
Shandong Provincial Key Laboratory of Tumor Imaging Equipment Development and Integrated Diagnosis and Treatment Technology, Institute of Biochemical Analysis, Linyi University, Lin Yi 276000, Shandong China.
The differences in the spatial structures of chiral enantiomers often lead to variations in physiological activity. Focusing on the stereoselective behavior of chiral enantiomers, timely and accurate risk assessment has become an important issue in pharmaceutical research development. The development of high-selectivity and rapid discrimination detection methods is the key to chiral enantiomer-related research.
View Article and Find Full Text PDFJ Am Chem Soc
September 2025
Department of Chemistry, Rice University, Houston, Texas 77005, United States.
Aminoglycoside antibiotics are one of the oldest and most clinically relevant classes of anti-infective agents, yet their complex molecular architectures have restricted access through bottom-up syntheses for decades. Herein we report enantioselective syntheses of 2-deoxyfortamine-type aminoglycosides sannamycins A and B. The described strategy involves an enantioselective dearomative hydroamination, rapid stereo- and chemoselective introduction of heteroatom functionalities, and a unique skeletal rearrangement to forge the aminocyclitol core.
View Article and Find Full Text PDFACS Med Chem Lett
August 2025
Department of Radiology, Molecular Imaging Innovations Institute (MI3), Weill Cornell Medicine, New York, New York 10065, United States.
The microglial lipid-sensing receptor TREM2 is a promising therapeutic target for Alzheimer's disease. We report the discovery of , a racemic structural analog of the clinical-stage TREM2 agonist . Synthesized via a concise, modular, and enantioselective-free route using sequential Suzuki couplings, enables rapid scaffold diversification.
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