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