The intramolecular Diels-Alder reaction of an ester-tethered 1,3,9-decatriene system was significantly accelerated in ionic liquids such as [emim]BF(4), [bmim]BF(4) and [bdmim]BF(4). Under the present conditions, the IMDA reaction proceeded smoothly without the use of Lewis acid catalysts to give cis-fused bicyclic lactones in good yield with high diastereoselectivity.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/b910488g | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Total Syntheses of Diepoxy-Kaurane Diterpenoids Enabled by a Bridgehead-Enone-Initiated Intramolecular Cycloaddition.
J Am Chem Soc
December 2024
State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
Here, we report the enantioselective total syntheses of four diepoxy--kaurane diterpenoids including (-)-Macrocalin B, (-)-Acetyl-macrocalin B, and (-)-Isoadenolin A and the revised structure of (-)-Phyllostacin I, which hinges on the strategic design of a regioselective and stereospecific trapping of a highly reactive [3.2.1]-bridgehead enone intermediate via a tethered intramolecular Diels-Alder reaction.
View Article and Find Full Text PDFTotal Synthesis of (+)-Mannolide B.
J Am Chem Soc
December 2024
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, and Chemical Biology Center, Peking University, 38 Xueyuan Road, Beijing 100191, China.
Article Synopsis
- (+)-Mannolide B features a complex hexacyclic structure with multiple stereocenters, presenting challenges for its total synthesis.
- A successful strategy involved ring-closing metathesis starting from (-)-methyl jasmonate to construct its tetracyclic carbon skeleton.
- The synthesis included various attempts, ultimately culminating in a Pauson-Khand reaction and a Büchner-Curtius-Schlotterbeck reaction, leading to the first total synthesis of (+)-mannolide B in 24 steps.
Divergent Access to Polycyclic Fluorenofuran Systems via Palladium-Catalyzed Cascade Furan-Participated Diels-Alder Cycloaddition Reactions.
Org Lett
December 2024
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University, Nanjing 211800, China.
The Pd-catalyzed reaction of 1-(2-iodophenyl)-3-arylprop-2-yn-1-ones with benzene-tethered furan-ynes produces novel fused hexacyclic indenone-furan scaffolds, while the reaction with propargyl furfuryl ethers affords the pentacyclic indenone-spirodifuran system. The thiophene-containing alkynes also proceed by similar transformations. A mechanism involving the Pd-catalyzed coupling and propargylic Alder-ene reaction to generate the indenone-allene intermediate, followed by an intramolecular furan/thiophene-participated inverse electron-demand Diels-Alder reaction, is proposed.
View Article and Find Full Text PDFSynthetic Study toward Daphnimacropodines.
Org Lett
December 2024
Department of Chemistry and Shenzhen Grubbs Institute and Guangdong Provincial Key Laboratory of Catalysis and Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Southern University of Science and Technology, Shenzhen 518055, Guangdong, China.
Daphnimacropodines A-C are members of a small but structurally distinct subfamily of alkaloids. Their congested polycyclic skeletons, and two vicinal quaternary stereocenters, present significant synthetic challenges. This paper describes two stereoselective approaches to constructing the tricyclic core structures of daphnimacropodines, achieved through a straightforward Rh-catalyzed [4 + 3] cycloaddition using simple building blocks.
View Article and Find Full Text PDFSynthesis of Substituted Tetralins via Nitrogen Deletion/Diels-Alder Cascade Reaction.
J Org Chem
December 2024
Department of Chemistry, Xi'an Jiaotong-Liverpool University, Suzhou 215123, China.
Skeletal editing is an important approach for the modification and diversification of biologically active molecules. The utilization of nitrogen deletion strategies in skeletal editing has recently emerged as a new method for compound modification. Here, we report an unexpected nitrogen deletion in isoindolines.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!