edoc

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

Zhang, Qi and Rinkel, Jan and Goldfuss, Bernd and Dickschat, Jeroen S. and Tiefenbacher, Konrad K. . (2018) Sesquiterpene cyclizations catalysed inside the resorcinarene capsule and application in the short synthesis of isolongifolene and isolongifolenone. Nature Catalysis , 1. pp. 609-615.

[img] PDF - Accepted Version
562Kb

Official URL: https://edoc.unibas.ch/68398/

Downloads: Statistics Overview

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. However, natural cyclase enzymes 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 examples of sesquiterpene cyclizations 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 cyclization reaction was elucidated using 13 C-labelling studies and density functional theory calculations.
Faculties and Departments:05 Faculty of Science > Departement Chemie
05 Faculty of Science > Departement Chemie > Chemie > Synthesis of Functional Modules (Tiefenbacher)
UniBasel Contributors:Zhang, Qi and Tiefenbacher, Konrad Karl
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Springer Nature
e-ISSN:2520-1158
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
Identification Number:
Last Modified:11 Jul 2019 12:48
Deposited On:24 Jan 2019 18:37

Repository Staff Only: item control page