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A concise synthesis of the 1,4-diarylbutanoid-phenethylamine alkaloids, schwarzinicines A () and B (), recently isolated from , is reported. Key steps include a Claisen condensation to assemble the 1,4-diaryl-2-butanone intermediate, followed by a reductive amination to furnish the core skeleton of the target compounds. The overall synthetic yields of and were 9.1% and 3.5%, respectively. Synthetic (-)-, (+)- and (±)- exhibited comparable vasorelaxation as natural schwarzinicine A on rat isolated aortic rings, suggesting that the observed vasorelaxant effects were not influenced by the chirality at C-2.
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http://dx.doi.org/10.1080/14786419.2021.1903005 | DOI Listing |
Org Lett
September 2025
State Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China.
A concise enantioselective total synthesis of (+)-lucidumone, a caged polycyclic meroterpenoid with a bicyclo[2.2.2]octane skeleton, was accomplished in 10 steps (LLS) starting from commercially available 2-cyclohexen-1-one.
View Article and Find Full Text PDFJ Org Chem
September 2025
Department of Radiation and Medical Oncology, Zhongnan Hospital of Wuhan University, School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, P. R. of China.
A Mg(OTf)-catalyzed asymmetric Michael addition/cyclization cascade reaction between 3-isothiocyanato oxindoles and 2-arylidene-1,3-indanediones has been developed. This transformation provides an efficient and concise approach to biologically important bispiro[indanedione-oxindole-pyrrolidinyl]s under mild conditions in good to excellent yields (70-99% yields) with moderate to good stereoselectivities (up to 99% and >95:5 d.r.
View Article and Find Full Text PDFCurr Top Med Chem
September 2025
Department of Mathematics and Natural Sciences, College of Sciences and Human Studies, Prince Mohammad Bin Fahd University, Al Khobar, Kingdom of Saudi Arabia.
Changes in the body's natural glucose levels have been associated with the onset of diabetes mellitus. It is frequently accompanied by a number of long-term consequences, including cardiovascular disease, retinopathy, nephropathy, and cataracts. Aldose reductase (AR), an enzyme belonging to the aldoketo reductase superfamily, plays a crucial role in the polyol pathway of glucose metabolism by converting glucose into sorbitol.
View Article and Find Full Text PDFOrg Lett
September 2025
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, Maharashtra, India.
A concise and efficient asymmetric total synthesis of bicyclic-THP-lactone natural products passifetilactone D and cryptorigidifoliol I and four of the stereoisomers of proposed cryptorigidifoliol B has been achieved, enabled by Maruoka/Reetz or Maruoka/Brown allylations and Ghosez lactonization. Although the required diastereomers of cryptorigidifoliol B are synthesized now, with the mismatch of data to that of the natural isolate, its actual structure could not be ascertained, indicating a need for further structure revision.
View Article and Find Full Text PDFJ Nat Prod
September 2025
Pharmaceutical College, Guangxi Medical University, Nanning, Guangxi 530021, PR China.
We describe two concise, three-step routes for the individual synthesis of 27-deoxywithaferin A () and 4--5,6-deoxywithaferin A () from withaferin A (). The protection strategy for the double bond of enone with thiophenol and the conjugate reduction of the epoxy group are important in generating these products, with an overall yield of 40%. The absolute configuration of 4--5,6-deoxywithaferin A () has been confirmed by X-ray crystallography.
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