Molecules 2013, 18(10), 12290-12312; doi:10.3390/molecules181012290
Review

The Piancatelli Rearrangement: New Applications for an Intriguing Reaction

1,* email and 2email
Received: 24 July 2013; in revised form: 18 September 2013 / Accepted: 23 September 2013 / Published: 8 October 2013
(This article belongs to the Special Issue Named Organic Reactions based on Italian Chemists)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: 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.
Keywords: 2-furylcarbinols; pentadienyl cation; prostaglandins; spirocycles; domino reaction
PDF Full-text Download PDF Full-Text [315 KB, uploaded 18 June 2014 20:12 CEST]

Export to BibTeX |
EndNote


MDPI and ACS Style

Piutti, C.; Quartieri, F. The Piancatelli Rearrangement: New Applications for an Intriguing Reaction. Molecules 2013, 18, 12290-12312.

AMA Style

Piutti C, Quartieri F. The Piancatelli Rearrangement: New Applications for an Intriguing Reaction. Molecules. 2013; 18(10):12290-12312.

Chicago/Turabian Style

Piutti, Claudia; Quartieri, Francesca. 2013. "The Piancatelli Rearrangement: New Applications for an Intriguing Reaction." Molecules 18, no. 10: 12290-12312.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert