Diastereoselective synthesis of functionalized 2-methyltetrahydropyran-4-ones

A simple procedure for the synthesis of functionalized 2-methyl-2,3-dihydropyran-4-ones, based on the Maitland–Japp reaction, and their diastereoselective conversion into functionalized 2-methyltetrahydropyran-4-ones has been developed. This allows access to a structural unit present in a large number of biologically active natural products, and has been successfully applied to the synthesis of the molecule found in Civet cat secretion.