Abstract
Terpenes constitute one of the most structurally varied classes of natural products. A wide range of these structures are produced in nature by type I terpene cyclase enzymes from one single substrate. However, such reactivity has proven difficult to reproduce in solution with man-made systems. Herein we report the shortest synthesis of the tricyclic sesquiterpene presilphiperfolan-1β-ol to date, utilizing the supramolecular resorcinarene capsule as catalyst for the key step. This synthetic approach also allows access to unnatural derivatives of the natural product, which would not be accessible through the biosynthetic machinery. Additionally, this study provides useful insight into the biosynthesis of the presilphiperfolanol natural products, including the first experimental evidence consistent with the proposed biosynthetic connection between caryophyllene and the presilphiperfolanols.
Original language | English |
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Pages (from-to) | 5894-5900 |
Number of pages | 7 |
Journal | Journal of the American Chemical Society |
Volume | 142 |
Issue number | 12 |
DOIs | |
State | Published - 25 Mar 2020 |
Bibliographical note
Funding Information:This work was supported by funding from the European Research Council Horizon 2020 Programme [ERC Starting Grant 714620-TERPENECAT] and the Swiss National Science Foundation as part of the NCCR Molecular Systems Engineering.
Publisher Copyright:
Copyright © 2020 American Chemical Society.