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Sesquiterpene Cyclisations Catalysed inside the Resorcinarene Capsule and Application in the Short Synthesis of Isolongifolene and Isolongifolenone.

ABSTRACT: Terpenes constitute the largest class of natural products and serve as an important source for medicinal treatments. Despite constant progress in chemical synthesis, the construction of complex polycyclic sesqui- and diterpene scaffolds remains challenging. Natural cyclase enzymes, however, are able to form the whole variety of terpene structures from just a handful of linear precursors. Man-made catalysts able to mimic such natural enzymes are lacking. Here, we describe the examples of sesquiterpene cyclisations inside an enzyme-mimicking supramolecular catalyst. This strategy allowed the formation of the tricyclic sesquiterpene isolongifolene in only four steps. The mechanism of the catalysed cyclisation reaction was elucidated using 13C-labelling studies and DFT calculations.

SUBMITTER: Zhang Q

PROVIDER: S-EPMC6130823 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Sesquiterpene Cyclisations Catalysed inside the Resorcinarene Capsule and Application in the Short Synthesis of Isolongifolene and Isolongifolenone.

Zhang Qi Q Rinkel Jan J Goldfuss Bernd B Dickschat Jeroen S JS Tiefenbacher Konrad K

Nature catalysis 20180730 8

Terpenes constitute the largest class of natural products and serve as an important source for medicinal treatments. Despite constant progress in chemical synthesis, the construction of complex polycyclic sesqui- and diterpene scaffolds remains challenging. Natural cyclase enzymes, however, are able to form the whole variety of terpene structures from just a handful of linear precursors. Man-made catalysts able to mimic such natural enzymes are lacking. Here, we describe the examples of sesquite ...[more]

PMID: 30221250

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