Zuppolini, Simona (2013) Synthesis of bioactive natural product analogues. [Tesi di dottorato]
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| Item Type: | Tesi di dottorato |
|---|---|
| Resource language: | English |
| Title: | Synthesis of bioactive natural product analogues |
| Creators: | Creators Email Zuppolini, Simona simona.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: | nome email Previtera, Lucio previter@unina.it |
| Tutor: | nome email Zarrelli, Armando zarrelli@unina.it |
| Date: | 2 April 2013 |
| Number of Pages: | 119 |
| 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 |
Collection description
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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