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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...
A highly enantioselective synthesis of functionalized tetrahydropyran-4-ones has been achieved by the development of a catalytic asymmetric Maitland–Japp reaction using Chan’s diene as the nucleophile. This reaction has been used to synthesize the tetrahydropyran ring of (−)-centrolobine and the C9–C19 tetrahydropyran ring of (+)-phorboxazole B.
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