Zuppolini, Simona (2013) Synthesis of bioactive natural product analogues. [Tesi di dottorato]

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Item Type: Tesi di dottorato
Lingua: English
Title: Synthesis of bioactive natural product analogues
Creators:
CreatorsEmail
Zuppolini, Simonasimona.zuppolini@unina.it
Date: 2 April 2013
Number of Pages: 119
Institution: Università degli Studi di Napoli Federico II
Department: Scienze Chimiche
Scuola di dottorato: Scienze chimiche
Dottorato: Scienze chimiche
Ciclo di dottorato: 25
Coordinatore del Corso di dottorato:
nomeemail
Previtera, Luciopreviter@unina.it
Tutor:
nomeemail
Zarrelli, Armandozarrelli@unina.it
Date: 2 April 2013
Number of Pages: 119
Uncontrolled Keywords: lignans, furan, triflic anhydride, Friedel-Crafts acylation, furanone, photooxygenation of furnas
Settori scientifico-disciplinari del MIUR: Area 03 - Scienze chimiche > CHIM/06 - Chimica organica
Date Deposited: 05 Apr 2013 06:19
Last Modified: 23 Jul 2014 09:47
URI: http://www.fedoa.unina.it/id/eprint/9458
DOI: 10.6092/UNINA/FEDOA/9458

Abstract

Easily accessible 2-aryl-3,4-dicarboxymethyl furans were recognized as starting precursors of 4-aroyl-2-phenyl furans, interesting products characterized by a 8-8’ linked C6C3-C3C6 backbone typical of lignans. A novel regiodivergent synthetic approach via trifluoromethanesulfonic anhydride (Tf2O)-mediated acylation is described. The reaction takes place under neat condition and at low temperatures. The procedure was also explored on 4-oxo-2-alkenoic acids, previously prepared by photooxygenation followed by basic treatment. Thus, 5,5- and 3,5-diarylfuranones have been obtained in a three-step one-pot manner.

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