Important tricyclic chemical compounds with efficient chirality control

Osaka University researchers developed a highly efficient way to produce chiral multi-centered fused tricyclic compounds of which core structure is often found in bioactive compounds including medicines.

Chemists have devoted tremendous efforts to develop a way to build molecules as they want. A single enantiomer (specific special arrangement of atoms) is essential for molecules of specific biomedical properties because of chiral nature of biological receptor sites (usually proteins). A very challenging goal in organic chemistry is asymmetric synthesis, selective preparation of a single enantiomer of a molecule.

Recently, chemists at Osaka University has synthesized highly enantioselective polycyclic chiral compounds with multiple chiral centers in an elegant and selective manner that could open new avenues in research and industry.

In their report in Nature Communications, the Osaka team focused to develop a novel and practical way to synthesize tricyclic molecules, named hydronaphthofurans. These scaffolds are abundant in natural products of important biological activities. The representative members of this family are morphine, azadirachtin, teucvidin and momilacton that are well-known to show a range of biological activities such as analgesic, anti-tumor, insecticides, and allelochemicals. Although some are found in nature, preparing them in the synthetic laboratory with the complete control of selectivity is a major challenge to the synthetic chemists.

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