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Concise Synthesis of (-)-Veratramine and (-)-20--Veratramine via Aromative Diels-Alder Reaction.
J Am Chem Soc
January 2025
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.
A concise and convergent synthesis of the isosteroidal alkaloids veratramine and 20--veratramine has been accomplished. A Horner-Wadsworth-Emmons olefination joins two chiral building blocks of approximately equal complexity and a transition-metal catalyzed intramolecular Diels-Alder cycloaddition-aromatization cascade constructs the tetrasubstituted arene. Other key steps include a highly diastereoselective crotylation of an -sulfonyl iminium ion and an Eschenmoser fragmentation.
View Article and Find Full Text PDFAsymmetric Total Syntheses of Sarglamides A, C, and E.
J Org Chem
January 2025
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000 Gansu, P. R. China.
The asymmetric total syntheses of sarglamides A, C, and E in concise and protecting group free fashion is disclosed. Key steps involve an -selective Diels-Alder reaction to construct the bicyclo[2.2.
View Article and Find Full Text PDFTotal Syntheses of Diepoxy-Kaurane Diterpenoids Enabled by a Bridgehead-Enone-Initiated Intramolecular Cycloaddition.
J Am Chem Soc
January 2025
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
January 2025
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.
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