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Pd(II)-catalyzed cyclization of alkyne-tethered malononitriles nitrile insertion.
Chem Commun (Camb)
January 2025
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
Herein, we have developed a Pd(II)-catalyzed cyclization of prochiral alkyne-tethered malononitriles to access five-membered carbocycles having a nitrile-containing all-carbon quaternary center. The reaction pathway involves a -acetoxypalladation, nitrile group insertions into the carbon-palladium bond and sequential deacetylation followed by -acetylation. Initial studies on asymmetric cyclization were also performed with chiral Pyox ligands.
View Article and Find Full Text PDFFrom Monocyclization to Pentacyclization: A Versatile Plant Cyclase Produces Diverse Sesterterpenes with Anti-Liver Fibrosis Potential.
Adv Sci (Weinh)
January 2025
State Key Laboratory of Southwestern Chinese Medicine Resources, and Innovative Institute of Chinese Medicine and Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, 611137, P. R. China.
A prolific multi-product sesterterpene synthase CbTPS1 is characterized from the medicinal Brassicaceae plant Capsella bursa-pastoris. Twenty different sesterterpenes including 16 undescribed compounds, possessing 10 different mono-/di-/tri-/tetra-/penta-carbocyclic skeletons, including the unique 15-membered macrocyclic and 24(15→14)-abeo-capbuane scaffolds, are isolated and structurally elucidated from engineered Escherichia coli strains expressing CbTPS1. Site-directed mutagenesis assisted by molecular dynamics simulations resulted in the variant L354M with up to 13.
View Article and Find Full Text PDFSynthesis, structure and π-expansion of tris(4,5-dehydro-2,3:6,7-dibenzotropone).
Beilstein J Org Chem
January 2025
Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China.
The polycyclic skeleton of tris(4,5-dehydro-2,3:6,7-dibenzotropone) is a key structural fragment in carbon schwarzites, a theoretical form of negatively curved carbon allotrope. This report presents a new synthesis of this compound using a Ni-mediated Yamamoto coupling reaction and structural analysis of it with X-ray crystallography. Interestingly, it is observed that tris(4,5-dehydro-2,3:6,7-dibenzotropone) crystallized from its solution in hexane resulting in colorless and yellow crystal polymorphs, where it adopts conformations of approximate and symmetry, respectively.
View Article and Find Full Text PDFRh-Catalyzed -Divinylcyclopropane Rearrangement: An Approach to 1,5-Disubstituted 1,4-Cycloheptadienes.
Org Lett
January 2025
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.
Under mild conditions and without the need of inert gas protection, a Rh-catalyzed rearrangement of -divinylcyclopropanes to form 1,5-disubstituted 1,4-cycloheptadienes has been developed and is disclosed here. This reaction can expedite the synthesis of challenging seven-membered carbocycles.
View Article and Find Full Text PDF()-2-Benzylidenecyclanones: Part XX-Reaction of Cyclic Chalcone Analogs with Cellular Thiols: Unexpected Increased Reactivity of 4-Chromanone- Compared to 1-Tetralone Analogs in Thia-Michael Reactions.
Molecules
November 2024
Institute of Pharmaceutical Chemistry, University of Pécs, H-7624 Pécs, Hungary.
In vitro relative cytotoxicity (IC ()/IC () of ()-3-(4'-methylbenzylidene)-4-chromanone () towards human Molt 4/C8 and CEM T-lymphocytes showed a >50-fold increase in comparison to those of the respective tetralone derivative (). On the other hand, such an increase was not observed in the analogous 4-OCH ( and ) derivatives. In order to study whether thiol reactivity-as a possible basis of the mechanism of action-correlates with the observed cytotoxicities, the kinetics of the non-enzyme catalyzed reactions with reduced glutathione (GSH) and N-acetylcysteine (NAC) of and were investigated.
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