An elegant total synthesis is sometimes as much a scientific achievement as it is a piece of art. And the last piece of art to date is the synthesis of Canataxpropellane, a member of the taxane diterpene family isolated in 2007, by T. Gaich and coworkers. It is undoubtedly one of the most complex natural products ever isolated and features 2 propellane units, 12 contiguous stereocenters and a cyclobutane with all quaternary stereocenters, along with many other synthetic challenges. The synthesis developed here relies on an impressive Diels-Alder/ortho-alkene-arene photocycloaddition sequence to build its core structure. Overall, the synthesis was achieved in 26 steps with a 0.5% yield and seems robust enough to prepare grams of the natural product for biological and pharmaceutical investigations. Noteworthy, a new chiral siloxane directing group was also developed during this study for the Diels-Alder reaction.
The ingenuity of synthetic chemists who manage to tackle such complexity is nothing but amazing. A big congratulations to Prof. Dr. Tanja Gaich and her team for this incredible achievement!

https://science.sciencemag.org/content/367/6478/676

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