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. Our group recently reported that a hexameric resorcinarene capsule can mimic terpene synthase enzymes by catalysing the tail-to-head terpene cyclization reaction. Additionally, we used this system to prepare a number of monoterpenes (such as α-terpinene and eucalyptol) and sesquiterpenes (such as isolongifolene and δ-selinene). However, these are commercially available compounds; to showcase the applicability of supramolecular catalysis to natural product synthesis, it would be highly desirable to identify capsule-catalyzed cascade reactions that lead to complex biologically active terpenes, difficult to access by other means. In this context, we will present here our studies 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.

Biomimetic four-step access to the sesquiterpene natural product presilphiperfolan-1β-ol via supramolecular catalysis

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.