Asymmetric Total Synthesis of Taxol

Closing the ring on Taxol

28 February 2022

A new method for assembling the highly complex molecule Taxol could help uncover even more potent derivatives of the anticancer drug.

Taxol is used in chemotherapy for treating various cancers, including breast, ovarian and lung cancers.

Taxol’s intricate chemical structure, which features a tetracyclic core richly decorated with oxygen functionality, has attracted the attention of some of the greatest synthetic organic chemists. However, until now, no routes used to assemble this formidable molecule have involved closing the central eight-membered ring by forming a new bond between the two carbon atoms designated C1 and C2 in the structure.

Now, a team led by researchers from SUSTech has shown that a ring-closing reaction mediated by samarium iodide can be used to form the C1–C2 bond. Their concise approach to the total synthesis of Taxol assembled the molecule in 19 isolated steps.

The new route offers new possibilities for synthesising novel derivates of the Taxol structure, with potentially enhanced medicinal properties.

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References

1. Journal of the American Chemical Society 143, 17862–17870 (2021). doi: 10.1021/jacs.1c09637