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Concise Synthesis of Naphthalene-Based 14-Aza-12-Oxasteroids.
Molecules
January 2025
Department of Chemistry, Acadia University, Wolfville, NS B4P 2R6, Canada.
A concise, transition metal-free four-step synthetic pathway has been developed for the synthesis of tetracyclic heterosteroidal compounds, 14-aza-12-oxasteroids, starting from readily available 2-naphthol analogues. After conversion of 2-naphthols to 2-naphthylamines by the Bucherer reaction, subsequent selective C-acetylation was achieved via the Sugasawa reaction and reduction of the acetyl group using borohydride, which resulted into the corresponding amino-alcohols. The naphthalene-based amino-alcohols underwent double dehydrations and double intramolecular cyclization with oxo-acids leading to one-pot formation of a C-N bond, a C-O bond and an amide bond in tandem, to generate two additional rings completing the steroidal framework.
View Article and Find Full Text PDFSynergistic Cu(II)/Amine-Catalyzed Cyclization of Enynone: Assembly of Tetralone and Tetrahydronaphthylimine.
Org Lett
January 2025
School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201, China.
An unprecedented synergistic copper- and amine-catalyzed cyclization of enynone is reported. This reaction features an efficient and straightforward construction of multisubstituted tetralone through an amine-assisted regioselective oxygen atom transfer process and stereoselective intramolecular Michael addition cyclization. Under dehydrative reaction conditions, the synthesis of tetrahydronaphthylimine derivatives with ketone group tolerance is achieved, which could be challenging via traditional methods.
View Article and Find Full Text PDFSynthesis of Oxabicyclo[3.2.1]octan-3-ol Scaffold via Burgess Reagent Mediated Cyclodehydration of δ-Diols under Acidic Conditions.
Org Lett
January 2025
Department of Chemistry, Department of Molecular Biosciences, Chemistry of Life Processes Institute, Center for Developmental Therapeutics, Northwestern University, Evanston, Illinois 60208-3113, United States.
Dehydrative cyclization of δ-diols was achieved by using the Burgess reagent under mild conditions to furnish a novel oxabicyclo[3.2.1]octan-3-ol scaffold.
View Article and Find Full Text PDFVisible-Light-Induced Annulation of Benzothioamides with Sulfoxonium Ylides To Construct Thiazole Derivatives.
Org Lett
January 2025
Innovation Center for Chemical Sciences, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou Industrial Park, Suzhou, Jiangsu 215123, China.
Herein, visible-light-induced annulation of benzothioamides with sulfoxonium ylides to furnish thiazole derivatives is developed under transition-metal-, photocatalyst-, and oxidant-free conditions. This protocol exhibits good substrate scope, affording the desired products with satisfied yields in a mild and green manner. Detailed mechanistic studies suggest that the benzothioamide substrate plays a dual role in this reaction.
View Article and Find Full Text PDFGenome mining of nonenzymatic ortho-quinone methide-based pseudonatural products from ascidian-derived fungus Diaporthe sp.SYSU-MS4722.
Bioorg Chem
January 2025
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:
Article Synopsis
- Ortho-quinone methides (o-QMs) are reactive intermediates formed from clavatol that lead to pseudonatural products (PNPs) in fungi, which can have significant biological activities.
- Genome mining identified a clavatol biosynthetic gene cluster (BGC) in the Diaporthe sp. SYSU-MS4722 fungus, allowing for the heterologous expression of key genes in Aspergillus oryzae NSAR1, leading to the discovery of 13 new clavatol-based PNPs.
- Structural analysis using various spectroscopic techniques confirmed the identities of these compounds, revealing several with notable anti-fibrotic activity.
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