Terpenes are amongst the most structurally varied classes of natural products, and much of this variety arises from the complex cyclization/rearrangement cascade reactions catalysed by type I terpene synthase enzymes. Man-made, non-enzymatic catalysts able to promote this reactivity are currently lacking; the Tiefenbacher group recently reported that a hexameric resorcinarene capsule can mimic terpene synthase enzymes by catalysing the tail-to-head terpene cyclization reaction.<br/>In the first part of this talk, I will present studies carried out in the Tiefenbacher group on the synthesis of the complex sesquiterpene presilphiperfolan-1β-ol in four steps from inexpensive, commercially available starting material, employing the resorcinarene capsule as the catalyst for the key step. Importantly, in addition to the natural product itself, this approach provides access to unnatural analogues that would be inaccessible using the biosynthetic machinery. In the second part of the talk, I will present work carried out jointly between the Tiefenbacher and Burke groups, aimed at a systematic exploration of the different cyclization modalities accessible via the resorcinarene capsule catalyst.

Synthesis of natural and unnatural sesquiterpenes via supramolecular catalysis

ACS Fall 2021

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