Bridging the gap between supramolecular chemistry and current synthetic challenges: Developing artificial catalysts for the tail-to-head terpene cyclization

Project Information

TERPENECAT

Grant agreement ID: 714620

DOI

10.3030/714620

Project closed

EC signature date 30 October 2016

Start date 1 November 2016

End date 31 October 2021

Funded under

• EXCELLENT SCIENCE - European Research Council (ERC)

Total cost

€ 1 500 000,00

EU contribution

€ 1 500 000,00

Coordinated by

UNIVERSITAT BASEL
Switzerland

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Publications

Peer reviewed articles (14)

Sesquiterpene Cyclizations inside the Hexameric Resorcinarene Capsule: Total Synthesis of δ‐Selinene and Mechanistic Studies

Author(s): Qi Zhang, Konrad Tiefenbacher
Published in: Angewandte Chemie International Edition, Issue 58/36, 2019, Page(s) 12688-12695, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201906753

Concentration-Dependent Self-Assembly of an Unusually Large Hexameric Hydrogen-Bonded Molecular Cage

Author(s): Severin Merget, Lorenzo Catti, Shani Zev, Dan T. Major, Nils Trapp, Konrad Tiefenbacher
Published in: Chemistry - A European Journal, 2021, ISSN 1521-3765
Publisher: Wiley-VCH
DOI: 10.1002/chem.202005046

Requirements for Terpene Cyclizations inside the Supramolecular Resorcinarene Capsule: Bound Water and Its Protonation Determine the Catalytic Activity

Author(s): Severin Merget, Lorenzo Catti, GiovanniMaria Piccini, Konrad Tiefenbacher
Published in: Journal of the American Chemical Society, Issue 142/9, 2020, Page(s) 4400-4410, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.9b13239

Molecular Capsule Catalysis: Ready to Address Current Challenges in Synthetic Organic Chemistry?

Author(s): Ivana Némethová, Leonidas-Dimitrios Syntrivanis, Konrad Tiefenbacher
Published in: CHIMIA International Journal for Chemistry, Issue 74/7, 2020, Page(s) 561-568, ISSN 0009-4293
Publisher: Schweizerische Chemische Gedellschaft
DOI: 10.2533/chimia.2020.561

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

Author(s): Leonidas-Dimitrios Syntrivanis, Ivana Némethová, Dario Schmid, Shani Levi, Alessandro Prescimone, Fabian Bissegger, Dan T. Major, Konrad Tiefenbacher
Published in: Journal of the American Chemical Society, Issue 142/12, 2020, Page(s) 5894-5900, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.0c01464

Brønsted Acid-Catalyzed Carbonyl-Olefin Metathesis inside a Self-Assembled Supramolecular Host

Author(s): Lorenzo Catti, Konrad Tiefenbacher
Published in: Angewandte Chemie International Edition, 2018, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201712141

Chirality Induction from a Chiral Guest to the Hydrogen-Bonding Network of Its Hexameric Resorcinarene Host Capsule

Author(s): Corina H. Pollok, Qi Zhang, Konrad Tiefenbacher, Christian Merten
Published in: ChemPhysChem, Issue 18/15, 2017, Page(s) 1987-1991, ISSN 1439-4235
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/cphc.201700610

Terpene Cyclizations inside a Supramolecular Catalyst: Leaving-Group-Controlled Product Selectivity and Mechanistic Studies

Author(s): Qi Zhang, Lorenzo Catti, Jürgen Pleiss, Konrad Tiefenbacher
Published in: Journal of the American Chemical Society, Issue 139/33, 2017, Page(s) 11482-11492, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.7b04480

Elucidating the Importance of Hydrochloric Acid as a Cocatalyst for Resorcinarene-Capsule-Catalyzed Reactions

Author(s): Jesper M. Köster, Konrad Tiefenbacher
Published in: ChemCatChem, 2018, ISSN 1867-3880
Publisher: Wiley - VCH Verlag GmbH & CO. KGaA
DOI: 10.1002/cctc.201800326

En route to terpene natural products utilizing supramolecular cyclase mimetics

Author(s): Qi Zhang, Lorenzo Catti, Leonidas-Dimitrios Syntrivanis, Konrad Tiefenbacher
Published in: Natural Product Reports, 2019, ISSN 0265-0568
Publisher: Royal Society of Chemistry
DOI: 10.1039/c9np00003h

Sesquiterpene cyclizations catalysed inside the resorcinarene capsule and application in the short synthesis of isolongifolene and isolongifolenone

Author(s): Qi Zhang, Jan Rinkel, Bernd Goldfuss, Jeroen S. Dickschat, Konrad Tiefenbacher
Published in: Nature Catalysis, Issue 1/8, 2018, Page(s) 609-615, ISSN 2520-1158
Publisher: Springer Nature Publishing AG
DOI: 10.1038/s41929-018-0115-4

Discovering Monoterpene Catalysis Inside Nanocapsules with Multiscale Modeling and Experiments

Author(s): Efrat Pahima, Qi Zhang, Konrad Tiefenbacher, Dan T. Major
Published in: Journal of the American Chemical Society, Issue 141/15, 2019, Page(s) 6234-6246, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.8b13411

Catalysis inside the Hexameric Resorcinarene Capsule

Author(s): Qi Zhang, Lorenzo Catti, Konrad Tiefenbacher
Published in: Accounts of Chemical Research, Issue 51/9, 2018, Page(s) 2107-2114, ISSN 0001-4842
Publisher: American Chemical Society
DOI: 10.1021/acs.accounts.8b00320

Optimized iminium-catalysed 1,4-reductions inside the resorcinarene capsule: achieving >90% ee with proline as catalyst

Author(s): Daria Sokolova, Konrad Tiefenbacher
Published in: RSC Advance, 2021, ISSN 2046-2069
Publisher: Royal Society of Chemistry
DOI: 10.1039/d1ra04333a