The Piancatelli Rearrangement: New Applications for an Intriguing Reaction
Nearly forty years ago, at the University of Rome, Giovanni Piancatelli and co-workers discovered the acid-catalyzed water-mediated rearrangement of 2-furylcarbinols into 4-hydroxycyclopentenones. These motifs are core components of several pharmacologically active compounds and precursors of many n...
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| Format: | Article |
| Language: | English |
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MDPI AG
2013-10-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/18/10/12290 |
| _version_ | 1818310313689219072 |
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| author | Francesca Quartieri Claudia Piutti |
| author_facet | Francesca Quartieri Claudia Piutti |
| author_sort | Francesca Quartieri |
| collection | DOAJ |
| description | Nearly forty years ago, at the University of Rome, Giovanni Piancatelli and co-workers discovered the acid-catalyzed water-mediated rearrangement of 2-furylcarbinols into 4-hydroxycyclopentenones. These motifs are core components of several pharmacologically active compounds and precursors of many natural products. The main features of this reaction are the simple experimental conditions, the stereochemical outcome and the generality of the procedure. Consequently, a re-emergence of this reaction has been seen recently, including developments of the Piancatelli rearrangement with some interesting inter- and intramolecular variants. This review will mainly focus on the general aspects of the reaction along with its more recent applications. |
| first_indexed | 2024-12-13T07:44:05Z |
| format | Article |
| id | doaj.art-68c65407a85e4d59adaeb8d1c2123d64 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-13T07:44:05Z |
| publishDate | 2013-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-68c65407a85e4d59adaeb8d1c2123d642022-12-21T23:54:52ZengMDPI AGMolecules1420-30492013-10-011810122901231210.3390/molecules181012290The Piancatelli Rearrangement: New Applications for an Intriguing ReactionFrancesca QuartieriClaudia PiuttiNearly forty years ago, at the University of Rome, Giovanni Piancatelli and co-workers discovered the acid-catalyzed water-mediated rearrangement of 2-furylcarbinols into 4-hydroxycyclopentenones. These motifs are core components of several pharmacologically active compounds and precursors of many natural products. The main features of this reaction are the simple experimental conditions, the stereochemical outcome and the generality of the procedure. Consequently, a re-emergence of this reaction has been seen recently, including developments of the Piancatelli rearrangement with some interesting inter- and intramolecular variants. This review will mainly focus on the general aspects of the reaction along with its more recent applications.http://www.mdpi.com/1420-3049/18/10/122902-furylcarbinolspentadienyl cationprostaglandinsspirocyclesdomino reaction |
| spellingShingle | Francesca Quartieri Claudia Piutti The Piancatelli Rearrangement: New Applications for an Intriguing Reaction Molecules 2-furylcarbinols pentadienyl cation prostaglandins spirocycles domino reaction |
| title | The Piancatelli Rearrangement: New Applications for an Intriguing Reaction |
| title_full | The Piancatelli Rearrangement: New Applications for an Intriguing Reaction |
| title_fullStr | The Piancatelli Rearrangement: New Applications for an Intriguing Reaction |
| title_full_unstemmed | The Piancatelli Rearrangement: New Applications for an Intriguing Reaction |
| title_short | The Piancatelli Rearrangement: New Applications for an Intriguing Reaction |
| title_sort | piancatelli rearrangement new applications for an intriguing reaction |
| topic | 2-furylcarbinols pentadienyl cation prostaglandins spirocycles domino reaction |
| url | http://www.mdpi.com/1420-3049/18/10/12290 |
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