Four-Step Access to the Sesquiterpene Natural Product Presilphiperfolan-1β-ol and Unnatural Derivatives via Supramolecular Catalysis

Journal of the American Chemical Society
Leonidas-Dimitrios SyntrivanisKonrad Tiefenbacher

Abstract

Terpenes constitute one of the most structurally varied classes of natural products. A wide range of these structures are produced in nature by type I terpene cyclase enzymes from one single substrate. However, such reactivity has proven difficult to reproduce in solution with man-made systems. Herein we report the shortest synthesis of the tricyclic sesquiterpene presilphiperfolan-1β-ol to date, utilizing the supramolecular resorcinarene capsule as catalyst for the key step. This synthetic approach also allows access to unnatural derivatives of the natural product, which would not be accessible through the biosynthetic machinery. Additionally, this study provides useful insight into the biosynthesis of the presilphiperfolanol natural products, including the first experimental evidence consistent with the proposed biosynthetic connection between caryophyllene and the presilphiperfolanols.

References

Mar 1, 2002·Journal of Chemical Ecology·Azucena González-ColomaMatías Reina
Dec 19, 2002·Journal of the American Chemical Society·Liat Avram, Yoram Cohen
Aug 30, 2003·The Journal of Organic Chemistry·Chad E DavisRobert M Coates
Oct 1, 2008·Organic Letters·Selina C Wang, Dean J Tantillo
Feb 10, 2011·Chemical Communications : Chem Comm·Ke Zhou, Reuben J Peters
Feb 23, 2011·The Journal of Organic Chemistry·José E Barquera-Lozada, Gabriel Cuevas
Oct 24, 2012·Nature Chemistry·Sergey V Pronin, Ryan A Shenvi
Oct 1, 1994·Journal of Chemical Ecology·I G ColladoR Hernández-Galán
Apr 17, 2014·Current Opinion in Chemical Biology·Dan Thomas MajorMichal Weitman
Apr 29, 2014·Angewandte Chemie·Allen Y Hong, Brian M Stoltz
Feb 24, 2015·Nature Chemistry·Q Zhang, K Tiefenbacher
Mar 30, 2017·Journal of the American Chemical Society·Pengfei Hu, Scott A Snyder
Jun 8, 2017·Journal of the American Chemical Society·Qi ZhangKonrad Tiefenbacher
Aug 26, 2017·Chemical Reviews·David W Christianson
Aug 29, 2018·Accounts of Chemical Research·Qi ZhangKonrad Tiefenbacher
Mar 26, 2019·Journal of the American Chemical Society·Efrat PahimaDan T Major
Apr 26, 2019·Natural Product Reports·Qi ZhangKonrad Tiefenbacher

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Citations

Dec 30, 2020·Angewandte Chemie·Monika ChwastekAgnieszka Szumna
May 20, 2021·Chemical Society Reviews·Giorgio OlivoStefano Di Stefano
Apr 22, 2021·Chemistry : a European Journal·Ricard López-CollAgustí Lledó
Jun 17, 2020·Journal of Natural Products·Georgijs StakanovsAigars Jirgensons
Oct 1, 2021·Journal of the American Chemical Society·David A PooleJoost N H Reek

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