A novel approach for the synthesis of unsaturated 7-membered lactones by Pd-catalyzed [5+2] dipolar cycloaddition of vinylethylene carbonates (VECs) and C5-substituted Meldrum's acid derivatives has been developed. Various Meldrum's acid derivatives worked well in this reaction under mild reaction conditions. A variety of 7-membered lactones can be accessed in a facile manner in moderate to good yields by employing easily prepared Meldrum's acid derivatives.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/d3cc05819k | DOI Listing |
To discriminate amino acid isomers by multiple stage tandem mass spectrometry (MS), the fragmentation of protonated amino acids were investigated by MS with collision-induced dissociation (CID) and density functional theory calculations. The CID of protonated α-amino acids results in a loss of 46 Da, corresponding to HO and CO, and iminium ions appear as resultant fragments. The CID of protonated β-amino acids also produces iminium ions, but the corresponding loss is 60 Da instead of 46 Da.
View Article and Find Full Text PDFCarbohydr Res
November 2024
Instituto de Ciencias Básicas, Universidad Veracruzana, Luis Castelazo Ayala, Col. Industrial Ánimas, CP 91190, Xalapa, Ver., Mexico. Electronic address:
A stereoselective synthesis of fused tricyclic framework of epi-parvistemonine A from D-glucono-δ-lactone is described. The synthetic strategic is based on the stereoselective construction of the 7-membered cyclic skeleton via a cross-metathesis reaction followed by a Michael type cyclization promoted by TfO.
View Article and Find Full Text PDFOrg Lett
August 2024
The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
Herein we report a strategy for the enantioselective synthesis of spirocycles containing all-carbon quaternary centers via nickel-catalyzed intramolecular addition of lactone enolates to aryl nitriles. The established lactone α-spirocyclization efficiently and enantioselectively forges 5-, 6-, and 7-membered rings, performing best in the synthesis of 7-membered rings (up to 90% ee). This discovery represents an expansion of the synthetic toolkit for enantioselective spirocyclization, providing access to chiral, pharmaceutically relevant spirocyclic products.
View Article and Find Full Text PDFOrg Lett
April 2024
Department of Chemistry, New York University, New York, New York 10003, United States.
Lannotinidine G is a unique Lycopodium alkaloid that features a tricyclic [6/6/6] core with 3 contiguous stereocenters and a 1,3-diene moiety in addition to a 7-membered lactone. Herein, we disclose our efforts toward the synthesis of this natural product, which achieved the construction of the aza-tricyclic core with the correct configuration at its three stereocenters. Key features of our strategy include a highly diastereoselective Fráter-Seebach alkylation and Corey-Chaykovsky type epoxide formation, an unusual aziridinium-mediated ring contraction for the formation of the piperidine moiety, and a regioselective dienyne metathesis.
View Article and Find Full Text PDFChem Commun (Camb)
February 2024
School of Pharmacy, Changzhou University, Changzhou, Jiangsu Province 213164, China.
A novel approach for the synthesis of unsaturated 7-membered lactones by Pd-catalyzed [5+2] dipolar cycloaddition of vinylethylene carbonates (VECs) and C5-substituted Meldrum's acid derivatives has been developed. Various Meldrum's acid derivatives worked well in this reaction under mild reaction conditions. A variety of 7-membered lactones can be accessed in a facile manner in moderate to good yields by employing easily prepared Meldrum's acid derivatives.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!