Jiangrine-like scaffolds from biorenewable platforms

Practical and scalable enantioselective synthesis of (+)-majoranolide from Cyrene

“…Other groups that have investigated aldol reactions with Cyrene also limited their studies to aromatic aldehydes, [16][17][18] with the exception of Sperry and coworkers, who reported reactions of aliphatic aldehydes in 35-58% yield promoted by KF on alumina. 19 It was envisaged that the synthesis of the important alkylidene lactone natural products 1 and 2 would be possible if the crossed aldol condensation of Cyrene with aliphatic aldehydes could be improved, and the products were then subjected to a Baeyer-Villiger reaction. We now describe the optimisation of the aldol process for aliphatic aldehydes and subsequent Baeyer-Villiger reaction of exocyclic alkylidene derivatives providing a route to 1 and 2.…”

Catalytic Strategies for Levoglucosenone Production by Pyrolysis of Cellulose and Lignocellulosic Biomass

“…Its structural characteristics enable its use as a chiral template for the synthesis of natural and unnatural chemicals. The pseudoenantiomer isolevoglucosenone is also readily derived from LGO and used likewise. , LGO works as a scaffold for drug discovery, and its derivatives have shown anticancer, antitumor, and antimicrobial activities. ,− A controlled oxidation of LGO produces rare sugars that are not found in nature . The chemicals synthesized from LGO have been used for other purposes, including catalysts, ligands, and auxiliaries .…”