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Meleagrin B is a terpene-alkaloid hybrid natural product that contains both the conidiogenone and meleagrin scaffold. Their derivatives show diverse biological activities. We characterized the biosynthesis of (-)-conidiogenone B (), which involves a diterpene synthase and a P450 monooxygenase. In addition, an α,β-hydrolase (Con-ABH) was shown to catalyze an aza-Michael addition between and imidazole to give -imidazolyl conidiogenone B (). Compound was more potent than against strains.
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http://dx.doi.org/10.1021/acs.orglett.1c00330 | DOI Listing |
J Org Chem
September 2025
Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal, Madya Pradesh 462 066, India.
Catalytic asymmetric total synthesis of the naturally occurring alkaloids, (-)-elwesine (), (-)-dihydrooxocrinine (), and (-)--crinine () bearing the characteristic 5,10-ethanophenanthridine framework has been reported. The synthesis features a key CBS reduction to generate an enantioenriched allylic alcohol (97% ee), followed by an Johnson-Claisen [3,3]-sigmatropic rearrangement to construct a sterically demanding all-carbon quaternary center at the pseudobenzylic position. Subsequent allylic oxidation furnishes the corresponding enone intermediate .
View Article and Find Full Text PDFJ Org Chem
August 2025
Biomass-derived Functional Oligosaccharides Engineering Technology Research Center of Anhui Province, School of Chemistry and Material Engineering, Fuyang Normal University, Fuyang 236037, China.
A facile catalyst-free regioselective 1,6-aza-Michael addition of -quinone methides with tetrazoles was efficiently developed using water as a green solvent. This process exhibited broad substrate compatibility, including benzotriazole, pyrazole, and indazole, yielding the corresponding -substituted azoles with excellent efficiency and regioselectivity. To demonstrate the practicality of this methodology, gram-scale reactions were successfully conducted.
View Article and Find Full Text PDFOrg Lett
August 2025
Borch Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, Indiana 47906, United States.
Modifications of morphine have delivered novel opioid scaffolds, such as 5-phenylmorphans and -octahydroisoquinolines, that exhibit various pharmacological profiles. To date, these substructures have only been prepared using chiral resolution strategies that require purging of 50% of the material at a late stage of a synthesis. Herein, we disclose the first enantioselective synthesis of both scaffolds.
View Article and Find Full Text PDFOrg Lett
August 2025
Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Guangxi Key Laboratory of Chemistry and Molecular Engineering of Medicinal Resources & Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical S
An efficient synthetic method to rapidly assemble the indole scaffold from an -aminobenzyl-substituted alkynyl-containing conjugated system was reported. This one-pot procedure involves an intramolecular aza-Michael addition followed by spontaneous alkene isomerization, affording the annulation product structurally characterized with an electron-withdrawing group on the C2 side chain. The developed methodology is conducted under mild reaction conditions and has broad substrate scope, wherein conjugated aldehyde, ketone, ester, amide, phosphonate, and sulfone are all amenable substrates.
View Article and Find Full Text PDFPolymers (Basel)
June 2025
Soprema, 15 Rue de Saint-Nazaire, 67100 Strasbourg, France.
This study focuses first on the synthesis through an aza-Michael addition reaction of original linear diamine prepolymers and original amine/acrylate thermoset adhesives, and second on their thermal, mechanical and adhesion characterization. The major advantage of the aza-Michael addition reaction is that it takes place at room temperature, without a solvent and without a catalyst. Using the aza-Michael addition reaction, linear secondary diamine prepolymers were first synthesized with a control of the molecular weight, ranging from 867 to 1882 g mol.
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