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Four-Step Access to the Sesquiterpene Natural Product Presilphiperfolan-1β-ol and Unnatural Derivatives via Supramolecular Catalysis

preprint
submitted on 23.09.2019 and posted on 26.09.2019 by Leonidas-Dimitrios Syntrivanis, Shani Levi, Alessandro Prescimone, Dan Thomas Major, Konrad Tiefenbacher
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 direct experimental evidence for the proposed biosynthetic connection between caryophyllene and the presilphiperfolanols.

Funding

NCCR MSE: Molecular Systems Engineering (phase II)

Swiss National Science Foundation

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ERC Starting Grant 714620- TERPENECAT

History

Email Address of Submitting Author

konrad.tiefenbacher@unibas.ch

Institution

University of Basel

Country

Switzerland

ORCID For Submitting Author

0000-0002-3351-6121

Declaration of Conflict of Interest

No conflict of interest.

Exports