Facile synthesis of 3(2H)-furanones

Facile synthesis of 3(2H)-furanones A practical method for the synthesis of 3(2H)-furanones including the bullatenone was described. Intramolecular cyclization of 4-hydroxyalkynones in the presence of KOH affords the biologically potent furanones in moderate-to-good yield at room temperature. Synthesis of 4-hydroxyalkynones from the reaction of acid chloride and terminal alkyne in the presence of copper iodide at room temperature was also reported. Graphical abstract Keywords 3(2H)-furanones  4-Hydroxyalkynone  Annulation  Cu-catalysis  Bullatenone Introduction albicans and Cladosporium resinae belong to this 3(2H)- furanone class [9]. Other compounds having this subunit The 3(2H)-furanone ring system (Fig. 1) is an interesting also show wide spectrum of biological properties, includ- class of heterocyclic core that constitutes the central ring of ing antiproliferative [10], antiulcer [11], antiallergic [12], many of the natural products isolated from a variety of selective COX-2 inhibition [13], and selective MAO-B sources like sponges, algae, animals, plants, and insects inhibition activities [14]. [1–4]. Jatrophone, eremantholides, geiparvarin, and parvi- Synthetic approaches to the 3(2H)-furanone ring system floranine A are some of the natural products of this class which vary in their degree of flexibility have been inves- that show potent anti-tumor activity [5–7]. The biological tigated by several groups. In 1971, Margaretha [15] property http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Monatshefte für Chemie - Chemical Monthly Springer Journals

Facile synthesis of 3(2H)-furanones

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Publisher
Springer Vienna
Copyright
Copyright © 2018 by Springer-Verlag GmbH Austria, part of Springer Nature
Subject
Chemistry; Chemistry/Food Science, general; Organic Chemistry; Inorganic Chemistry; Analytical Chemistry; Physical Chemistry; Theoretical and Computational Chemistry
ISSN
0026-9247
eISSN
1434-4475
D.O.I.
10.1007/s00706-018-2152-8
Publisher site
See Article on Publisher Site

Abstract

A practical method for the synthesis of 3(2H)-furanones including the bullatenone was described. Intramolecular cyclization of 4-hydroxyalkynones in the presence of KOH affords the biologically potent furanones in moderate-to-good yield at room temperature. Synthesis of 4-hydroxyalkynones from the reaction of acid chloride and terminal alkyne in the presence of copper iodide at room temperature was also reported. Graphical abstract Keywords 3(2H)-furanones  4-Hydroxyalkynone  Annulation  Cu-catalysis  Bullatenone Introduction albicans and Cladosporium resinae belong to this 3(2H)- furanone class [9]. Other compounds having this subunit The 3(2H)-furanone ring system (Fig. 1) is an interesting also show wide spectrum of biological properties, includ- class of heterocyclic core that constitutes the central ring of ing antiproliferative [10], antiulcer [11], antiallergic [12], many of the natural products isolated from a variety of selective COX-2 inhibition [13], and selective MAO-B sources like sponges, algae, animals, plants, and insects inhibition activities [14]. [1–4]. Jatrophone, eremantholides, geiparvarin, and parvi- Synthetic approaches to the 3(2H)-furanone ring system floranine A are some of the natural products of this class which vary in their degree of flexibility have been inves- that show potent anti-tumor activity [5–7]. The biological tigated by several groups. In 1971, Margaretha [15] property

Journal

Monatshefte für Chemie - Chemical MonthlySpringer Journals

Published: Feb 15, 2018

References

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