Universität zu Köln

Zhang, Qi, Rinkel, Jan, Goldfuss, Bernd ORCID: 0000-0002-1814-8818, Dickschat, Jeroen S. and Tiefenbacher, Konrad ORCID: 0000-0002-3351-6121 (2018). Sesquiterpene cyclizations catalysed inside the resorcinarene capsule and application in the short synthesis of isolongifolene and isolongifolenone. Nat. Catal., 1 (8). S. 609 - 616. LONDON: NATURE PUBLISHING GROUP. ISSN 2520-1158

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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 C-13-labelling studies and density functional theory calculations.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Zhang, Qi UNSPECIFIED UNSPECIFIED UNSPECIFIED Rinkel, Jan UNSPECIFIED UNSPECIFIED UNSPECIFIED Goldfuss, Bernd UNSPECIFIED orcid.org/0000-0002-1814-8818 UNSPECIFIED Dickschat, Jeroen S. UNSPECIFIED UNSPECIFIED UNSPECIFIED Tiefenbacher, Konrad UNSPECIFIED orcid.org/0000-0002-3351-6121 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-177449
DOI:	10.1038/s41929-018-0115-4
Journal or Publication Title:	Nat. Catal.
Volume:	1
Number:	8
Page Range:	S. 609 - 616
Date:	2018
Publisher:	NATURE PUBLISHING GROUP
Place of Publication:	LONDON
ISSN:	2520-1158
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language REARRANGEMENT; ENCAPSULATION; BIOSYNTHESIS; CHEMISTRY; MECHANISM; TERPENES; FARNESOL; STEREOCHEMISTRY; NEROLIDOL; EXCHANGE Multiple languages Chemistry, Physical Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/17744