Biomimetic tail-to-head terpene cyclizations using the resorcin[4]arene capsule catalyst

Ivan Cornu, Leonidas-Dimitrios Syntrivanis, Konrad Tiefenbacher

Published: 2023-12-01 DOI: 10.1038/s41596-023-00919-3

Biomimetic THT cyclizations

Resorcin[4]arene capsule

Terpene synthesis

Capsule catalyst

Carbocationic rearrangements

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References

Introduction
Materials
Procedure 1: synthesis of resorcin[4]arene
- Section 1: synthesis of dry resorcin[4]arene
- Section 2: synthesis of wet resorcin[4]arene
Procedure 2: cyclization with a specific low water content: synthesis of isolongifolene
Procedure 3: presilphiperfolan-1β-ol
- Section 1: screening-scale synthesis of presilphiperfolan-1β-ol
- Section 2: preparative synthesis of presilphiperfolan-1β-ol
Troubleshooting
Timing
Anticipated results
Acknowledgements
Extended Data Fig. 1 HCl stock solution preparation.
Extended Data Fig. 2 HCl stock solution titration.
Extended Data Fig. 3 Resorcin[4]arene synthesis.
Extended Data Fig. 4 Photo of the resorcin[4]arene stock solution prepared in Steps 9–17 of Procedure 2.
Extended Data Fig. 5 Dissolution of resorcin[4]arene in water-saturated chloroform.
Extended Data Fig. 6 Reaction setup.

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Biomimetic tail-to-head terpene cyclizations using the resorcin[4]arene capsule catalyst

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