Prof. Dr. Konrad Tiefenbacher Department of Chemistry Profiles & Affiliations OverviewResearch Publications Projects & Collaborations Projects & Collaborations OverviewResearch Publications Projects & Collaborations Profiles & Affiliations Projects & Collaborations 11 foundShow per page10 10 20 50 Biomimetic methyl transfers to alkenes to initiate polyene cyclizations. Can a methyl cation” initiate alkene cyclizations in a similar manner to a proton? Research Project | 1 Project MembersImported from Grants Tool 4683321 Advancing catalysis inside supramolecular capsules: Proton wire substrate activation, overcoming the size limitation, and enantioselective catalysis. Research Project | 1 Project MembersNo Description available Synthesis of sulfabutanoic acid (SBA) derivatives Research Project | 1 Project MembersNo Description available NCCR Catalysis Research, Call1_KT Research Project | 1 Project MembersNCCR Catalysis Research, Call 1 KT Endowing Bio-Membranes with Orthogonal Function by Incorporating Supramolecular Modules Research Project | 3 Project MembersNo Description available PROTEAS - Programming Terpene Cyclization Through Iterative Precursor Assembly Research Project | 2 Project MembersRecent advances in the development of iterative synthetic methodology ("assembly-line synthesis") have the potential to bring about a paradigm shift in small molecule synthesis, by providing automated protocols similar to those used for oligopeptide and oligonucleotide synthesis. However, a clear limitation of such systems has been the synthesis of topologically complex frameworks. Drawing inspiration from Nature, this project aims to address this issue by providing an innovative protocol for the automated synthesis of complex natural product-like scaffolds. This will be done by combining two cutting-edge methodologies: (i) the automated synthetic platform developed by the Burke group in the University of Illinois at Urbana-Champaign, which can rapidly provide libraries of small molecules by the iterative coupling of N-methyliminodiacetic acid (MIDA) boronate building blocks, and (ii) a novel supramolecular capsule catalyst developed by the Tiefenbacher group at the University of Basel, which has the unique capability to catalyse the tail-to-head terpene cyclization, the same transformation employed by Nature to give rise to the myriad of known terpene structures. The Burke group's small molecule synthesizer will thus be used to rapidly assemble linear terpenoid precursors, which will then be subjected to tail-to-head terpene cyclization via the Tiefenbacher group's catalyst to form cyclized terpenoid structures. The project will identify factors that influence the course of the cyclization and develop methods to control it so that desired scaffolds are produced on-demand. At its conclusion, it aims to provide a platform for the automated preparation of natural product-like compounds that will greatly impact chemical biology and medicinal chemistry research. NCCR Molecular Systems Engineering - phase 2 Research Project | 30 Project MembersMolecular Systems Engineering is a National Centre of Competence in Research (NCCR) funded by the Swiss National Science Foundation (SNSF), and headed by the University of Basel and the ETH Zurich. This NCCR combines expertise from chemistry, biology, physics, bioinformatics, and engineering. The overreaching aim is to develop tools and devices to monitor and manipulate off-equilibrium (bio)chemical systems. These may find applications in the synthesis of high added-value products, as innovative diagnostic tools and for the restoration of a desired cellular or organ function. Tackling Current Limitations of the Supramolecular Resorcinarene Capsule Catalyst: Compatibility with Water, Size, and Anionic Reactions Research Project | 1 Project MembersNo Description available TERPENECAT Research Project | 1 Project MembersBridging the gap between supramolecular chemistry and current synthetic challenges: Developing artificial catalysts for the tail-to-head terpene cyclization Nature is a rich source of biologically active molecules, among which the largest and most diverse group of natural products are terpenes. Essential drugs like the cancer medication taxol/paclitaxel or the malaria drug artemisinin belong to the terpene family. They are efficiently formed in nature through a so-called tail-to-head terpene cyclization. Chemists are not able to mimic this process with man-made catalysts. This proposal aims at closing this significant research gap by utilizing supramolecular chemistry. Learning how to design such complex catalysts will not only enable us to mimic natural enzymes, but to enter uncharted territory of terpene chemistry. The main objective is the development of selective catalysts for terpene cyclizations. This certainly poses the greatest challenge within this proposal. Therefore, two independent work packages were devised to tackle this challenge. A novel class of self-assembled catalysts will be developed which are able to control the conformation of the substrate, thereby allowing for selectivity in the cyclization process. The active site of these catalysts can be modified to selectively produce the desired terpene product. Additionally, dynamic covalent chemistry will be employed to construct covalent catalyst structures. As the second objective, this proposal aims to greatly expand the natural variety of terpenes by utilizing unnatural terpene cyclization precursors. Utilizing the catalysts developed from objective 1, unprecedented artemisinin drug derivatives, which are not accessible via other routes, will be synthesized. This project will provide catalysts which are able to predictably constrain the conformation of the substrate. Such control is not possible with state-of-the-art catalyst systems. Therefore, I anticipate that this project will open up new horizons in the fields of catalysis and organic synthesis. Scalable Total Synthesis of biologically interesting Natural products via late stage CH-Oxidation Research Project | 1 Project MembersNo Description available 12 12 OverviewResearch Publications Projects & Collaborations
Projects & Collaborations 11 foundShow per page10 10 20 50 Biomimetic methyl transfers to alkenes to initiate polyene cyclizations. Can a methyl cation” initiate alkene cyclizations in a similar manner to a proton? Research Project | 1 Project MembersImported from Grants Tool 4683321 Advancing catalysis inside supramolecular capsules: Proton wire substrate activation, overcoming the size limitation, and enantioselective catalysis. Research Project | 1 Project MembersNo Description available Synthesis of sulfabutanoic acid (SBA) derivatives Research Project | 1 Project MembersNo Description available NCCR Catalysis Research, Call1_KT Research Project | 1 Project MembersNCCR Catalysis Research, Call 1 KT Endowing Bio-Membranes with Orthogonal Function by Incorporating Supramolecular Modules Research Project | 3 Project MembersNo Description available PROTEAS - Programming Terpene Cyclization Through Iterative Precursor Assembly Research Project | 2 Project MembersRecent advances in the development of iterative synthetic methodology ("assembly-line synthesis") have the potential to bring about a paradigm shift in small molecule synthesis, by providing automated protocols similar to those used for oligopeptide and oligonucleotide synthesis. However, a clear limitation of such systems has been the synthesis of topologically complex frameworks. Drawing inspiration from Nature, this project aims to address this issue by providing an innovative protocol for the automated synthesis of complex natural product-like scaffolds. This will be done by combining two cutting-edge methodologies: (i) the automated synthetic platform developed by the Burke group in the University of Illinois at Urbana-Champaign, which can rapidly provide libraries of small molecules by the iterative coupling of N-methyliminodiacetic acid (MIDA) boronate building blocks, and (ii) a novel supramolecular capsule catalyst developed by the Tiefenbacher group at the University of Basel, which has the unique capability to catalyse the tail-to-head terpene cyclization, the same transformation employed by Nature to give rise to the myriad of known terpene structures. The Burke group's small molecule synthesizer will thus be used to rapidly assemble linear terpenoid precursors, which will then be subjected to tail-to-head terpene cyclization via the Tiefenbacher group's catalyst to form cyclized terpenoid structures. The project will identify factors that influence the course of the cyclization and develop methods to control it so that desired scaffolds are produced on-demand. At its conclusion, it aims to provide a platform for the automated preparation of natural product-like compounds that will greatly impact chemical biology and medicinal chemistry research. NCCR Molecular Systems Engineering - phase 2 Research Project | 30 Project MembersMolecular Systems Engineering is a National Centre of Competence in Research (NCCR) funded by the Swiss National Science Foundation (SNSF), and headed by the University of Basel and the ETH Zurich. This NCCR combines expertise from chemistry, biology, physics, bioinformatics, and engineering. The overreaching aim is to develop tools and devices to monitor and manipulate off-equilibrium (bio)chemical systems. These may find applications in the synthesis of high added-value products, as innovative diagnostic tools and for the restoration of a desired cellular or organ function. Tackling Current Limitations of the Supramolecular Resorcinarene Capsule Catalyst: Compatibility with Water, Size, and Anionic Reactions Research Project | 1 Project MembersNo Description available TERPENECAT Research Project | 1 Project MembersBridging the gap between supramolecular chemistry and current synthetic challenges: Developing artificial catalysts for the tail-to-head terpene cyclization Nature is a rich source of biologically active molecules, among which the largest and most diverse group of natural products are terpenes. Essential drugs like the cancer medication taxol/paclitaxel or the malaria drug artemisinin belong to the terpene family. They are efficiently formed in nature through a so-called tail-to-head terpene cyclization. Chemists are not able to mimic this process with man-made catalysts. This proposal aims at closing this significant research gap by utilizing supramolecular chemistry. Learning how to design such complex catalysts will not only enable us to mimic natural enzymes, but to enter uncharted territory of terpene chemistry. The main objective is the development of selective catalysts for terpene cyclizations. This certainly poses the greatest challenge within this proposal. Therefore, two independent work packages were devised to tackle this challenge. A novel class of self-assembled catalysts will be developed which are able to control the conformation of the substrate, thereby allowing for selectivity in the cyclization process. The active site of these catalysts can be modified to selectively produce the desired terpene product. Additionally, dynamic covalent chemistry will be employed to construct covalent catalyst structures. As the second objective, this proposal aims to greatly expand the natural variety of terpenes by utilizing unnatural terpene cyclization precursors. Utilizing the catalysts developed from objective 1, unprecedented artemisinin drug derivatives, which are not accessible via other routes, will be synthesized. This project will provide catalysts which are able to predictably constrain the conformation of the substrate. Such control is not possible with state-of-the-art catalyst systems. Therefore, I anticipate that this project will open up new horizons in the fields of catalysis and organic synthesis. Scalable Total Synthesis of biologically interesting Natural products via late stage CH-Oxidation Research Project | 1 Project MembersNo Description available 12 12
Biomimetic methyl transfers to alkenes to initiate polyene cyclizations. Can a methyl cation” initiate alkene cyclizations in a similar manner to a proton? Research Project | 1 Project MembersImported from Grants Tool 4683321
Advancing catalysis inside supramolecular capsules: Proton wire substrate activation, overcoming the size limitation, and enantioselective catalysis. Research Project | 1 Project MembersNo Description available
Synthesis of sulfabutanoic acid (SBA) derivatives Research Project | 1 Project MembersNo Description available
NCCR Catalysis Research, Call1_KT Research Project | 1 Project MembersNCCR Catalysis Research, Call 1 KT
Endowing Bio-Membranes with Orthogonal Function by Incorporating Supramolecular Modules Research Project | 3 Project MembersNo Description available
PROTEAS - Programming Terpene Cyclization Through Iterative Precursor Assembly Research Project | 2 Project MembersRecent advances in the development of iterative synthetic methodology ("assembly-line synthesis") have the potential to bring about a paradigm shift in small molecule synthesis, by providing automated protocols similar to those used for oligopeptide and oligonucleotide synthesis. However, a clear limitation of such systems has been the synthesis of topologically complex frameworks. Drawing inspiration from Nature, this project aims to address this issue by providing an innovative protocol for the automated synthesis of complex natural product-like scaffolds. This will be done by combining two cutting-edge methodologies: (i) the automated synthetic platform developed by the Burke group in the University of Illinois at Urbana-Champaign, which can rapidly provide libraries of small molecules by the iterative coupling of N-methyliminodiacetic acid (MIDA) boronate building blocks, and (ii) a novel supramolecular capsule catalyst developed by the Tiefenbacher group at the University of Basel, which has the unique capability to catalyse the tail-to-head terpene cyclization, the same transformation employed by Nature to give rise to the myriad of known terpene structures. The Burke group's small molecule synthesizer will thus be used to rapidly assemble linear terpenoid precursors, which will then be subjected to tail-to-head terpene cyclization via the Tiefenbacher group's catalyst to form cyclized terpenoid structures. The project will identify factors that influence the course of the cyclization and develop methods to control it so that desired scaffolds are produced on-demand. At its conclusion, it aims to provide a platform for the automated preparation of natural product-like compounds that will greatly impact chemical biology and medicinal chemistry research.
NCCR Molecular Systems Engineering - phase 2 Research Project | 30 Project MembersMolecular Systems Engineering is a National Centre of Competence in Research (NCCR) funded by the Swiss National Science Foundation (SNSF), and headed by the University of Basel and the ETH Zurich. This NCCR combines expertise from chemistry, biology, physics, bioinformatics, and engineering. The overreaching aim is to develop tools and devices to monitor and manipulate off-equilibrium (bio)chemical systems. These may find applications in the synthesis of high added-value products, as innovative diagnostic tools and for the restoration of a desired cellular or organ function.
Tackling Current Limitations of the Supramolecular Resorcinarene Capsule Catalyst: Compatibility with Water, Size, and Anionic Reactions Research Project | 1 Project MembersNo Description available
TERPENECAT Research Project | 1 Project MembersBridging the gap between supramolecular chemistry and current synthetic challenges: Developing artificial catalysts for the tail-to-head terpene cyclization Nature is a rich source of biologically active molecules, among which the largest and most diverse group of natural products are terpenes. Essential drugs like the cancer medication taxol/paclitaxel or the malaria drug artemisinin belong to the terpene family. They are efficiently formed in nature through a so-called tail-to-head terpene cyclization. Chemists are not able to mimic this process with man-made catalysts. This proposal aims at closing this significant research gap by utilizing supramolecular chemistry. Learning how to design such complex catalysts will not only enable us to mimic natural enzymes, but to enter uncharted territory of terpene chemistry. The main objective is the development of selective catalysts for terpene cyclizations. This certainly poses the greatest challenge within this proposal. Therefore, two independent work packages were devised to tackle this challenge. A novel class of self-assembled catalysts will be developed which are able to control the conformation of the substrate, thereby allowing for selectivity in the cyclization process. The active site of these catalysts can be modified to selectively produce the desired terpene product. Additionally, dynamic covalent chemistry will be employed to construct covalent catalyst structures. As the second objective, this proposal aims to greatly expand the natural variety of terpenes by utilizing unnatural terpene cyclization precursors. Utilizing the catalysts developed from objective 1, unprecedented artemisinin drug derivatives, which are not accessible via other routes, will be synthesized. This project will provide catalysts which are able to predictably constrain the conformation of the substrate. Such control is not possible with state-of-the-art catalyst systems. Therefore, I anticipate that this project will open up new horizons in the fields of catalysis and organic synthesis.
Scalable Total Synthesis of biologically interesting Natural products via late stage CH-Oxidation Research Project | 1 Project MembersNo Description available
