The hydroxypyrroloindolenine (Hpi) motif forms the fundamental core of the pentacyclic natural product, brevianamide E, the concise stereoselective synthesis of which, via oxidative cyclization, is described.
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http://dx.doi.org/10.1021/ol202880y | DOI Listing |
Commun Chem
March 2025
Freie Universität Berlin, Institute of Chemistry and Biochemistry, Berlin, Germany.
The stereoselective introduction of glycosidic bonds is one of the greatest challenges in carbohydrate chemistry. A key aspect of controlling glycan synthesis is the glycosylation reaction in which the glycosidic linkages are formed. The outcome is governed by a reactive sugar intermediate - the glycosyl cation.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
March 2025
Dalhousie University, Department of Chemistry, Chemistry Building, 6274 Coburg Road, B3H 4R2, Halifax, CANADA.
Robust organic molecules that place functional groups at well-defined angular and radial separations are valued as connectors in synthetic chemistry. Examples include rigid, polyvalent arenes and bicyclic compounds featuring strong C-C or C-H bonds. Non-aromatic rings like cyclohexane are rare in this context due to the challenge of stereochemical control over C-H functionalization.
View Article and Find Full Text PDFOrg Biomol Chem
March 2025
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
We developed a novel synthetic route for the KRAS inhibitor, focusing on the efficient construction of its central quinoline scaffold. The method offers several advantages: eliminates the formation of regioselective by-products and avoids the use of high temperatures and nitric acid. The last step of the overall route enables gentle hydrolysis of phenyl esters with methanol and potassium carbonate, which greatly reduces the occurrence of side reactions.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
March 2025
Kunming Institute of Botany Chinese Academy of Sciences, State Key Laboratory of Phytochemistry and Plant Resources in West China, 132 Lanhei Road, 650201, Kunming, CHINA.
Stereoselective constructions of 1,2-cis-glycosidic bonds are long-standing challenges in chemical synthesis. In particular, achieving highly stereoselective 1,2-cis-xylosylation remains a difficult task in carbohydrates chemistry. Here, we report that highly stereoselective 1,2-cis-xylosylation could be achieved via synergistic combinations of reagent modulation, remote participation and electron-withdrawing effects.
View Article and Find Full Text PDFOrg Lett
March 2025
Department of Chemistry, Indiana University, Bloomington, Indiana 47405, United States.
A convergent route toward the synthesis of leiodolide A () is described. Our studies explored reactions of the indium chloride-induced transmetalation of allylic stannane for nucleophilic addition with nonracemic aldehyde . The stereoselective formation of the all- stereotriad was rationalized by an isomerization to produce the -allylindium reagent for subsequent -Felkin addition.
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