Focus

The main focus of the organic synthesis research group is the chemical synthesis and derivatisation of organic compounds with non-trivial carbon connectivities, such as those found in polycyclic Natural Products. The design and selection of target structures is guided by a specific interest in reactivity patterns and/or a specific interest in biological phenomena. This research often follows a substrate-driven approach which relies on the use of highly modular synthetic intermediates as versatile building blocks or chemical platforms for various applications.

  • The chemical synthesis research mainly involves the development of novel strategies and methods to assemble complex polycyclic scaffolds found in Nature, focusing on multiple bond forming steps such as cycloadditions and cascade reactions. [1], [2]
  • The chemical derivatisation research focuses on the development of application-oriented versatile covalent ligation reactions (such as click-type reactions) to generate multiple functional derivatives from simple substrates or synthetic intermediates. [3]
  • A major recent theme, which encompasses both of the above general topics, consists of research directed at the design and synthesis of highly modular synthetic building blocks that allow a rapid exploration of Natural Product-like chemical space using simple and orthogonal functional group transformations. [4]
  • The concepts of versatile ligation/functionalisation reactions and modular building blocks in organic synthesis are also explored and applied in various collaborative research projects ranging from macromolecular and materials science to chemical biology. [5], [6]

publications

Publications

Doing both independent work and collaborations.

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courses

Courses

Giving courses to BSc and MSc in chemistry

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people

People

Former and current people working in the group.

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contact

Contact

For questions, do not hesitate to contact us.

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Latest publications

The latest independent publications are given below, for all independent publications and collaborations, see publications

An Intramolecular Cycloaddition Approach to the Kauranoid Family of Diterpene Metabolites

An Intramolecular Cycloaddition Approach to the Kauranoid Family of Diterpene Metabolites

Synthetic studies toward the ent-kauranoid family of diterpene natural products are reported. An intramolecular (4 + 3) cycloaddition allows the direct elaboration of diverse natural product frameworks, encompassing a challenging bicyclo[3.2.1]octane core. The established routes comprise only a few synthetic operations (3–5 steps), transforming a range of simple starting materials into the tetracyclic scaffolds that are commonly found in many ent-kaurene metabolites.

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Stereoselective and Modular Assembly Method for Heterocycle-Fused Daucane Sesquiterpenoids

Stereoselective and Modular Assembly Method for Heterocycle-Fused Daucane Sesquiterpenoids

A stereoselective synthetic method is reported for the molecular framework found in common daucane and isodaucane sesquiterpenoid natural products. The synthetic method constitutes a scalable, modular, and also asymmetric access to a complex natural product scaffold, wherein the substitution pattern and the stereochemistry can be adjusted simply by choosing different starting materials. The method allows the rapid introduction of diverse heterocyclic substructures such as (benzo)furans, (benzo)thiophenes, dithiins, thiazoles, and indoles, which actually also facilitate and direct the key intramolecular annulation step.

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Heterocycles as Moderators of Allyl Cation Cycloaddition Reactivity

Heterocycles as Moderators of Allyl Cation Cycloaddition Reactivity

For the rapid elaboration of polycarbocyclic scaffolds, prevalent in many important families of terpenoid natural products, allyl cations derived from simple heterocyclic alcohols can be used as versatile reaction partners in both (4+3) and (3+2) cycloaddition pathways. Our recent progress in this area is outlined, pointing towards the untapped potential of heterocycles to act as reagents in novel or known but challenging organic transformations.

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(5,6-Dihydro-1,4-dithiin-2-yl)methanol as a Versatile Allyl-Cation Equivalent in (3+2) Cycloaddition Reactions

(5,6-Dihydro-1,4-dithiin-2-yl)methanol as a Versatile Allyl-Cation Equivalent in (3+2) Cycloaddition Reactions

The title heterocyclic alcohol readily generates a sulfur-substituted allylic cation upon simple treatment with a protic acid, thus facilitating a synthetically useful stepwise (3+2) cycloaddition reaction pathway with a range of conjugated-olefin-type substrates. The introduction of an allyl fragment in this way provided rapid access to a variety of cyclopentanoid scaffolds. The cyclic nature of the cation precursor alcohol was shown to be instrumental for efficient cycloaddition reactions to take place, thus indicating an attractive strategy for controlling the reactivity of heteroatom-substituted allyl cations. The formal cycloaddition reaction is highly regio- and stereoselective and was also used for a short total synthesis of the natural product cuparene in racemic form through a cycloaddition-hydrodesulfurization sequence.

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La Chimie crée son objet. Cette faculté créatrice, semblable a l’art lui-même, la distingue essentiellement de sciences naturelles et historiques.

Marcelin Berthelot, 1876